2-Acetamido-4-methylthiazole-5-sulfonyl chloride → HCID 86681531, compound

HRID 391869Notes

Reaction equation

HRID 391869 reaction equation
C(NC1SC(S(Cl)(=O)=O)=C(C)N=1)(=O)C.C[O:16][C:17](=[O:81])[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]([NH:57][C:58](=[O:67])[C:59]5[CH:64]=[CH:63][C:62]([Cl:65])=[C:61]([Cl:66])[CH:60]=5)=[CH:53][CH:52]=4)[O:50][C:42]3=[CH:41][C:40]=2[CH2:39][N:38]1[S:68]([C:71]1[S:75][C:74]([NH:76]C(=O)C)=[N:73][C:72]=1[CH3:80])(=[O:70])=[O:69])=[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>>[NH2:76][C:74]1[S:75][C:71]([S:68]([N:38]2[CH:37]([C:35]([NH:34][C@@H:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:27]=[CH:28][C:29]([C:32]#[N:33])=[CH:30][CH:31]=4)=[CH:22][CH:21]=3)[C:17]([OH:81])=[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:56]=[CH:55][C:54]([NH:57][C:58](=[O:67])[C:59]6[CH:64]=[CH:63][C:62]([Cl:65])=[C:61]([Cl:66])[CH:60]=6)=[CH:53][CH:52]=5)[O:50][C:42]4=[CH:41][C:40]=3[CH2:39]2)(=[O:70])=[O:69])=[C:72]([CH3:80])[N:73]=1

Participants

3

Reactant 2

HCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chlorideHCID 86681532HCID 86681532, compound

Product 1

HCID 86681531HCID 86681531, compound

Procedure

The methyl ester hydrochloride (10 mg) was reacted with 2-acetylamino-4-methyl thiazole-5-sulfonyl chloride (7 mg) according to General Procedure E. The resulting (S)-2-({(S)-7-(2-Acetylamino-4-methyl-thiazole-5-sulfonyl)-3-[4-(3,4-dichloro-benzoylamino)-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 (8 mg) was hydrolyzed according to General Procedures N and B to give the title compound. LCMS: (m/z) 924.

Sources & evidence

ORD record
ord-eecb00089e574947bb24885d54a4c46d
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

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