6-Aminobenzothiazole → 2-(2-Trifluoromethylphenylamino)-1H-benzoimidazole-5-carboxylic acid benzothiazol-6-ylamide

HRID 388967Notes

Reaction equation

HRID 388967 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([C:19](O)=[O:20])=[CH:18][C:12]=2[N:11]=1.[NH2:24][C:25]1[CH:33]=[CH:32][C:28]2[N:29]=[CH:30][S:31][C:27]=2[CH:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[S:31]1[C:27]2[CH:26]=[C:25]([NH:24][C:19]([C:17]3[CH:16]=[CH:15][C:13]4[NH:14][C:10]([NH:9][C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[C:2]([F:22])([F:23])[F:1])=[N:11][C:12]=4[CH:18]=3)=[O:20])[CH:33]=[CH:32][C:28]=2[N:29]=[CH:30]1

Participants

4

Reactant 3

HCID 682886-AminobenzothiazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524173HCID 178524173, compound

Product 1

HCID 1785217892-(2-Trifluoromethylphenylamino)-1H-benzoimidazole-5-carboxylic acid benzothiazol-6-ylamide

Procedure

The carboxylic acid obtained as above (0.25 mmol) was coupled with 6-aminobenzothiazole (0.25 mmol) using HBTU employing general procedure D. The product, 2-(2-Trifluoromethylphenylamino)-1H-benzoimidazole-5-carboxylic acid benzothiazol-6-ylamide, was obtained as a light brown solid after purification by silica gel chromatography using DCM/methanol as eluent. MS: m/z 454 (M+H)+.

Sources & evidence

ORD record
ord-682a08d4a85c4c78a235f119e5aa4df9
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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