2-Methylbenzothiazol-5-ylamine dihydrochloride → SB-782443

HRID 491570Notes

Reaction equation

HRID 491570 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([CH3:12])=[N:9][C:8]=2[CH:13]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[C:23]([CH3:30])[N:22]=2)=[CH:17][CH:16]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:29]=[CH:28][C:24]([C:25]([NH:3][C:4]3[CH:5]=[CH:6][C:7]4[S:11][C:10]([CH3:12])=[N:9][C:8]=4[CH:13]=3)=[O:26])=[C:23]([CH3:30])[N:22]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 162189432-Methylbenzothiazol-5-ylamine dihydrochlorideHCID 242777906-(4-Fluorophenyl)-2-methylpyridine-3-carboxylic acid

Product 1

HCID 9951636SB-782443

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-methylbenzothiazole dihydrochloride (98 mg, 0.41 mmol), 6-(4-fluorophenyl)-2-methylnicotinic acid (D3) (96 mg, 0.42 mmol), 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (119 mg, 0.62 mmol) and 4-dimethylaminopyridine (25 mg, 0.21 mmol) in DCM (2 ml) were stirred at room temperature overnight. The reaction mixture was purified directly by column chromatography, eluting with a 0-10% MeOH/DCM gradient to give the title compound as a white solid. 1H NMR (400 MHz, DMSO) δ (ppm): 8.42 (d, 1H), 8.21 (dd, 2H), 8.02 (d, 1H), 7.98 (d, 1H), 7.94 (d, 1H), 7.71 (dd, 1H), 7.34 (t, 2H), 2.80 (s, 3H), 2.67 (s, 3H). MS(ES): MH+ 378, M−H+ 376.

Workup

  1. customThe reaction mixture was purified directly by column chromatography
  2. washeluting with a 0-10% MeOH/DCM gradient

Sources & evidence

ORD record
ord-610ddc797c1f493a8a254e7c15264392
Source dataset
uspto-grants-2009_05
Patent number
US07531558B2

Reaction notes

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