{5-Aminomethyl-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester → 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-4,7-dihydro-5H-thiazolo[5,4-c]pyridin-6-one

HRID 1433083Notes

Reaction equation

HRID 1433083 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:7]=[C:8]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([S:20]([C:23]3[S:27][C:26]4[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:25]=4[CH:24]=3)(=[O:22])=[O:21])[CH2:16][C:15]2=[O:33])[S:9][C:10]=1[CH2:11][NH2:12])C>CCO>[Cl:32][C:29]1[CH:30]=[CH:31][C:25]2[CH:24]=[C:23]([S:20]([N:17]3[CH2:18][CH2:19][N:14]([CH2:13][C:8]4[S:9][C:10]5[CH2:11][NH:12][C:4](=[O:3])[CH2:5][C:6]=5[N:7]=4)[C:15](=[O:33])[CH2:16]3)(=[O:22])=[O:21])[S:27][C:26]=2[CH:28]=1

Participants

3

Reactant 1

HCID 69024621{5-Aminomethyl-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester

Product 1

HCID 670138552-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-4,7-dihydro-5H-thiazolo[5,4-c]pyridin-6-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

{5-Aminomethyl-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester (12 mg, 0.02 mmol) is heated in EtOH (3 mL) for 3 days at 70° C. The precipitate which is formed is filtered to provide 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-4,7-dihydro-5H-thiazolo[5,4-c]pyridin-6-one. 1H NMR (300 MHz, DMSO) δ8.31 (d, 1H), 8.08-8.02 (m, 2H), 7.55 (dd, 1H), 4.67 (s, 2H), 4.36 (s (broad), 2H), 3.84 (s, 2H), 3.60-3.54 (m, 4H), 3.38 (t, 2H); MS (LC/MS-ESI) 496 (M+H)+.

Workup

  1. customThe precipitate which is formed
  2. filtrationis filtered

Sources & evidence

ORD record
ord-9aecc558336b4a1592987902b15b05d9
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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