2-Acetamido-4-methylthiazole-5-sulfonyl chloride → HCID 86681533, compound
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:51])[C@@H:5]([NH:21][C:22]([CH:24]1[CH2:33][C:32]2[CH:31]=[C:30]3[O:34][CH2:35][C@H:36]([C:38]4[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH:46]5[CH2:50][CH2:49][CH2:48][CH2:47]5)=[CH:40][CH:39]=4)[O:37][C:29]3=[CH:28][C:27]=2[CH2:26][NH:25]1)=[O:23])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[C:52]([NH:55][C:56]1[S:57][C:58]([S:62](Cl)(=[O:64])=[O:63])=[C:59]([CH3:61])[N:60]=1)(=[O:54])[CH3:53]>>[CH3:2][O:3][C:4](=[O:51])[C@@H:5]([NH:21][C:22]([CH:24]1[CH2:33][C:32]2[CH:31]=[C:30]3[O:34][CH2:35][C@H:36]([C:38]4[CH:39]=[CH:40][C:41]([O:44][CH2:45][CH:46]5[CH2:47][CH2:48][CH2:49][CH2:50]5)=[CH:42][CH:43]=4)[O:37][C:29]3=[CH:28][C:27]=2[CH2:26][N:25]1[S:62]([C:58]1[S:57][C:56]([NH:55][C:52](=[O:54])[CH3:53])=[N:60][C:59]=1[CH3:61])(=[O:63])=[O:64])=[O:23])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=2)=[CH:9][CH:8]=1Participants
3
Procedure
(S)-3-(4′-Cyano-biphenyl-4-yl)-2-{[(S)-3-(4-cyclopentylmethoxy-phenyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-propionic acid methylester hydrochloride (18 mg) was reacted with 2-acetylamino-4-methyl thiazole-5-sulfonyl chloride (11 mg) according to General Procedure E to give (S)-2-{[(S)-7-(2-acetylamino-4-methyl-thiazole-5-sulfonyl)-3-(4-cyclopentylmethoxy-phenyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester (17 mg). This was hydrolyzed according to General Procedures N and B to give the title compound (4.5 mg). LCMS: (m/z) 835.
Sources & evidence
- ORD record
- ord-ac470dc32b844c829887c2921dab8817
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987295B2
Reaction notes
Loading…