2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-cyano-thiophen-3-yl)-phenoxy]-propyl]-thiazole-4-carboxylic acid → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-(2-phenyl-azetidin-1-ylmethyl)-thiazole-4-carboxylic acid

HRID 1518353Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:31]CCOC3C=CC(C4C(C#N)=CSC=4)=CC=3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12].[C:48]1([CH:54]2[CH2:57][CH2:56][N:55]2CC2SC(N3CCC4C(=C(C(=O)/C=C5/SC6C=CC=CC=6N/5COCC[Si](C)(C)C)C=CC=4)C3)=NC=2C(OC)=O)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[S:24][C:25]([CH2:31][N:55]3[CH2:56][CH2:57][CH:54]3[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

Reactant 2

HCID 468362452-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-cyano-thiophen-3-yl)-phenoxy]-propyl]-thiazole-4-carboxylic acid

HCID 59447568(E)-methyl 5-((2-phenylazetidin-1-yl)methyl)-2-(8-(2-(3-((2-(trimethylsilyl)ethoxy)methyl)benzo[d]thiazol-2(3H)-ylidene)acetyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

Product 1

HCID 468365732-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-(2-phenyl-azetidin-1-ylmethyl)-thiazole-4-carboxylic acid

Procedure

The title compound was prepared in a similar manner to the synthesis of compound 51 by substituting compound 51A with compound 71A: 1H NMR (DMSO-d6): δ 12.89 (s, 1H), 8.04 (d, J=7.36 Hz, 1H), 7.80 (d, J=7.98 Hz, 1H), 7.70 (d, J=7.37 Hz, 1H), 7.34-7.54 (m, 9H), 5.47 (br, 1H), 4.70-4.95 (m, 4H), 4.40 (br, s, 1H), 3.88 (br, 1H), 3.76 (d, J=5.83 Hz, 2H), 2.60-2.8 (br, s, 2H). ESI (+)/MS: 582 (M+H)+.

Sources & evidence

ORD record: ord-c6612f7cfee8403e804129548e06ca81
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232273B2

Reaction notes

Loading…