2-Isothiocyanato-3-methylpyridine → HCID 178426312, compound

HRID 388964Notes

Reaction equation

HRID 388964 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[CH:16][C:15]=2[C:22](=[O:33])[NH:23][C:24]2[CH:32]=[CH:31][C:27]3[N:28]=[CH:29][S:30][C:26]=3[CH:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:34]([C:37]1[C:42]([CH3:43])=[CH:41][CH:40]=[CH:39][N:38]=1)=[C:35]=S>C(Cl)CCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([C:22](=[O:33])[NH:23][C:24]3[CH:32]=[CH:31][C:27]4[N:28]=[CH:29][S:30][C:26]=4[CH:25]=3)=[CH:16][C:17]3[N:21]=[C:35]([NH:34][C:37]4[C:42]([CH3:43])=[CH:41][CH:40]=[CH:39][N:38]=4)[NH:20][C:18]=3[CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 215089102-Isothiocyanato-3-methylpyridineHCID 68444837HCID 68444837, compound

Product 1

HCID 178426312HCID 178426312, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-[4,5-diamino-2-(benzothiazol-6-ylcarbamoyl)-phenyl]piperazine-1-carboxylic acid tert-butyl ester (see Example 163; 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 4-[6-(Benzothiazol-6-ylcarbamoyl)-2-(3-methyl-pyridin-2-ylamino)-3H-benzoimidazol-5-yl]piperazine-1-carboxylic acid tert-butyl ester. MS: m/z 585 (M+H)+.

Sources & evidence

ORD record
ord-57faf0edd1674b9e86148ace9a4d4ae3
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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