4-Methyl-1,2,3-thiadiazole-5-carbonyl chloride → 4-Methyl-[1,2,3]thiadiazole-5-carboxylic Acid [2-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-benzo[b]thiophen-7-yl]-amide

HRID 1986661Notes

Reaction equation

HRID 1986661 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[C:8]([O:32][CH3:33])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[C:19](C4N=CC=CC=4C(N)=O)=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].COC1C=[N:43]C=C(C=1)C(O)=O.[CH3:50][C:51]1[N:52]=[N:53][S:54][C:55]=1[C:56](Cl)=[O:57]>>[C:1]([C:5]1[CH:6]=[C:7]([NH:34][S:35]([CH3:38])(=[O:36])=[O:37])[C:8]([O:32][CH3:33])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[C:19]([NH:43][C:56]([C:55]4[S:54][N:53]=[N:52][C:51]=4[CH3:50])=[O:57])=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 3

HCID 27369824-Methyl-1,2,3-thiadiazole-5-carbonyl chlorideHCID 47383905-Methoxynicotinic acidHCID 86590363[2-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-benzo[b]thiophen-7-yl]-nicotinamide

Product 1

HCID 577224214-Methyl-[1,2,3]thiadiazole-5-carboxylic Acid [2-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-benzo[b]thiophen-7-yl]-amideYield 50%

Procedure

Was prepared as described for -[2-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-benzo[b]thiophen-7-yl]-nicotinamide starting with 5-methoxy-nicotinic acid to provide 20 mg (50%) of the title compound 4-Methyl-[1,2,3]thiadiazole-5-carbonyl chloride.

Workup

  1. customWas prepared

Sources & evidence

ORD record
ord-cfa5c9644a9d45e5b6ed9100b4336125
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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