2-Acetamido-4-methylthiazole-5-sulfonyl chloride → HCID 86654910, compound

HRID 879779Notes

Reaction equation

HRID 879779 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:47])[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][CH3:46])=[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:48]([NH:51][C:52]1[S:53][C:54]([S:58](Cl)(=[O:60])=[O:59])=[C:55]([CH3:57])[N:56]=1)(=[O:50])[CH3:49]>>[CH3:2][O:3][C:4](=[O:47])[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][CH3:46])=[CH:42][CH:43]=4)[O:37][C:29]3=[CH:28][C:27]=2[CH2:26][N:25]1[S:58]([C:54]1[S:53][C:52]([NH:51][C:48](=[O:50])[CH3:49])=[N:56][C:55]=1[CH3:57])(=[O:59])=[O:60])=[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]=1

Participants

3

Reactant 2

HCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chlorideHCID 66719841HCID 66719841, compound

Product 1

HCID 86654910HCID 86654910, compoundYield 73.9%

Procedure

(S)-3-(4′-Cyano-biphenyl-4-yl)-2-{[(S)-3-(4-ethoxy-phenyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carbonyl]-amino}-propionic acid methyl ester 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-ethoxy-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 (5 mg). LCMS: (m/z) 783.

Sources & evidence

ORD record
ord-fa78dca8899442cfaa1e7694af0cd8ea
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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