2,1,3-Benzothiadiazol-4-amine → (2S,4EZ)-N2-(2,1,3-benzothiadiazol-4-yl)-N1-(3,5-dichlorophenyl)-4-(methoxyimino)-1,2-pyrrolidinedicarboxamide

HRID 1349131Notes

Reaction equation

HRID 1349131 reaction equation
C(O[C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][C@H:9]1[C:16]([OH:18])=O)=[O:7])(C)(C)C.[Cl:19][C:20]1[CH:25]=[C:24]([N:26]=C=O)[CH:23]=[C:22]([Cl:29])[CH:21]=1.[N:30]1[S:31][N:32]=[C:33]2[C:38]([NH2:39])=[CH:37][CH:36]=[CH:35][C:34]=12>>[N:30]1[S:31][N:32]=[C:33]2[C:38]([NH:39][C:16]([C@@H:9]3[CH2:10][C:11](=[N:13][O:14][CH3:15])[CH2:12][N:8]3[C:6]([NH:26][C:24]3[CH:25]=[C:20]([Cl:19])[CH:21]=[C:22]([Cl:29])[CH:23]=3)=[O:7])=[O:18])=[CH:37][CH:36]=[CH:35][C:34]=12

Participants

4

Reactant 3

HCID 698452,1,3-Benzothiadiazol-4-amineHCID 944603,5-Dichlorophenyl isocyanateHCID 58714586(2S,4EZ)-1(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid

Product 1

HCID 131725485(2S,4EZ)-N2-(2,1,3-benzothiadiazol-4-yl)-N1-(3,5-dichlorophenyl)-4-(methoxyimino)-1,2-pyrrolidinedicarboxamide

Procedure

Following the general method as outlined in Example 22, starting from (2S,4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid, 1,3-dichloro-5-isocyanatobenzene, and 2,1,3-benzothiadiazol-4-amine the title compound was obtained in 55% purity by LC/MS. MS(ESI+): m/z=479.6.

Sources & evidence

ORD record
ord-97e58fe4993846c4aa0037ba32d9c9c7
Source dataset
uspto-grants-2007_05
Patent number
US07211601B2

Reaction notes

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