How to say he tried in vain to solve the problem. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighそのその(sono) (n,n-suf) that/garden/orchard/park/plantation/place/location問題問題(mondai) (n) problem/questionを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,解こno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbうとしたno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbが(ga) (prt) indicates sentence subject/indicates possessive/but/however/still/and無駄無駄(muda) (adj-na,n) futility/uselessness/pointlessnessだっただった(datta) was。(。) Japanese period "."    
kareha sono mondai wo toko utoshitaga muda datta 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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2)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sighそのその(sono) (n,n-suf) that/garden/orchard/park/plantation/place/location問題問題(mondai) (n) problem/questionの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates questionためにために(tameni) for sake of/on behalf of/as a result of無駄無駄(muda) (adj-na,n) futility/uselessness/pointlessnessに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.疲れ疲れ(tsukare) (n) tiredness/fatigueた(ta) (aux-v) indicate past completed or action/indicates light imperative。(。) Japanese period "."    
kareha sono mondai notameni muda ni tsukare ta 。
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