2-Isothiocyanato-3-methylpyridine → HCID 178426310, compound

HRID 1163406Notes

Reaction equation

HRID 1163406 reaction equation
[NH2:1][C:2]1[C:19]([NH2:20])=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[O:7])=[C:4]([N:21]([CH3:23])[CH3:22])[CH:3]=1.[N:24]([C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=1)=[C:25]=S>C(Cl)CCl>[NH:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([NH:8][C:6]([C:5]3[C:4]([N:21]([CH3:23])[CH3:22])=[CH:3][C:2]4[NH:1][C:25]([NH:24][C:27]5[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][N:28]=5)=[N:20][C:19]=4[CH:18]=3)=[O:7])[CH:17]=2)[CH:13]=[N:14]1

Participants

4

Reactant 2

HCID 215089102-Isothiocyanato-3-methylpyridineHCID 68444802HCID 68444802, compound

Product 1

HCID 178426310HCID 178426310, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4,5-diamino-2-dimethylamino-N-(1H-indazol-6-yl)benzamide (see Example 160; 0.3 mmol) was reacted with 2-isothiocyanato-3-methylpyridine (0.3 mmol; prepared from 2-amino-3-methylpyridine and thiophosgene employing procedure described in Example 115) followed by cyclization in situ using EDC as described in general procedure B to provide 6-dimethylamino-2-(3-methylpyridin-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (1H-indazol-6-yl)-amide. MS: m/z 427 (M+H)+.

Sources & evidence

ORD record
ord-23f77c19afeb4be48c4415fa0697fc55
Source dataset
uspto-grants-2010_10
Patent number
US07820821B2

Reaction notes

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