How to say he ran and ran, but could not catch up with his dog. 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走り走り(hashiri) (n) the first of the season or yearに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.走った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犬(inu) (n) dog familiaris)/snoop/loser/asshole/counterfeit/inferior/useless/wastefulに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.no dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbい(i) (prt) strengthens a question, assertion, etc.つけなかったno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb。(。) Japanese period "."    
kareha hashiri ni hashitta ga inu ni oi tsukenakatta 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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