2-Acetamido-4-methylthiazole-5-sulfonyl chloride → HCID 86654911, compound
Reaction equation
C(NC1SC(S(Cl)(=O)=O)=C(C)N=1)(=O)C.C[O:16][C:17](=[O:78])[C@@H:18]([NH:34][C:35]([CH:37]1[CH2:46][C:45]2[CH:44]=[C:43]3[O:47][CH2:48][C@H:49]([C:51]4[CH:56]=[CH:55][C:54]([O:57][CH2:58][C:59]5[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=5)=[CH:53][CH:52]=4)[O:50][C:42]3=[CH:41][C:40]=2[CH2:39][N:38]1[S:65]([C:68]1[S:72][C:71]([NH:73]C(=O)C)=[N:70][C:69]=1[CH3:77])(=[O:67])=[O:66])=[O:36])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1>>[NH2:73][C:71]1[S:72][C:68]([S:65]([N:38]2[CH:37]([C:35]([NH:34][C@@H:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]4[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=4)=[CH:24][CH:25]=3)[C:17]([OH:78])=[O:16])=[O:36])[CH2:46][C:45]3[CH:44]=[C:43]4[O:47][CH2:48][C@H:49]([C:51]5[CH:52]=[CH:53][C:54]([O:57][CH2:58][C:59]6[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=6)=[CH:55][CH:56]=5)[O:50][C:42]4=[CH:41][C:40]=3[CH2:39]2)(=[O:67])=[O:66])=[C:69]([CH3:77])[N:70]=1Participants
3
Procedure
(S)-2-{[(S)-3-(4-Benzyloxy-phenyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino-[2,3g]-isoquinoline-8-carbonyl]-amino}-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester hydrochloride was reacted with 2-acetylamino-4-methyl thiazole-5-sulfonyl chloride according to General Procedure E. The resulting (S)-2-{[(S)-7-(2-Acetylamino-4-methyl-thiazole-5-sulfonyl)-3-(4-benzyloxy-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 (18 mg) was hydrolyzed according to General Procedures N and B to the title compound (5 mg). LCMS (m/z) 843.
Sources & evidence
- ORD record
- ord-ed2ad2d6ec0148f3bfd97bee3bb6463c
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383644B2
Reaction notes
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