4-(3-Fluoro-benzyl)-5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester → 4-(3-Fluoro-benzyl)-5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid isopropyl ester

HRID 902500Notes

Reaction equation

HRID 902500 reaction equation
[CH:1]([O:4][C:5]([C:7]1[C:12](=[O:13])[N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:10]2[CH:22]=[CH:23][S:24][C:9]=2[C:8]=1Cl)=[O:6])([CH3:3])[CH3:2].C(OC(C1C(=O)N(CC2C=CC=C(F)C=2)C2C=CSC=2C=1[N:49]1[CH2:54][CH2:53][N:52]([C:55]([C:57]2[S:58][CH:59]=[CH:60][CH:61]=2)=[O:56])[CH2:51][CH2:50]1)=O)C>>[CH:1]([O:4][C:5]([C:7]1[C:12](=[O:13])[N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:10]2[CH:22]=[CH:23][S:24][C:9]=2[C:8]=1[N:49]1[CH2:54][CH2:53][N:52]([C:55]([C:57]2[S:58][CH:59]=[CH:60][CH:61]=2)=[O:56])[CH2:51][CH2:50]1)=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 118526974-(3-Fluoro-benzyl)-5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl esterHCID 693141127-Chloro-4-(3-fluoro-benzyl)-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid isopropyl ester

Product 1

HCID 597021034-(3-Fluoro-benzyl)-5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid isopropyl ester

Procedure

This compound was prepared from 7-chloro-4-(3-fluoro-benzyl)-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid isopropyl ester (18) by applying the same procedure as described for 4-(3-fluoro-benzyl)-5-oxo-7-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (9). Yield (57%). 1H-NMR (DMSO-d6) δ 1.29 (d, J=6.4 Hz, 6H), 3.37 (m, 4H), 3.81 (m, 4H), 5.10 (m, 1H), 5.38 (s, 2H), 7.04-7.16 (m, 4H), 7.32 (d, J=5.6 Hz, 1H), 7.37 (m, 1H), 7.47 (dd, J=1.2, 3.6 Hz, 1H), 7.79 (dd, J=1.2, 5.2 Hz, 1H), 8.02 (d, J=5.6 Hz, 1H); EIMS m/z 540 (M+1).

Workup

  1. customYield (57%)

Sources & evidence

ORD record
ord-260ef21deaac4af28e7bfd18277b246e
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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