Potassium Carbonate → 7-chloro-6-[(2-cyclohexyl-benzothiazol-6-yl-methyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 911396Notes

Reaction equation

HRID 911396 reaction equation
[NH2:1][C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[Cl:19].Br[CH2:21][C:22]1[CH:36]=[CH:35][C:25]2[N:26]=[C:27]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[S:28][C:24]=2[CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:19][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][N:9]([C:13](=[O:18])[C:14]([F:17])([F:15])[F:16])[CH2:10][CH2:11][C:12]=2[C:2]=1[NH:1][CH2:21][C:22]1[CH:36]=[CH:35][C:25]2[N:26]=[C:27]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[S:28][C:24]=2[CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 576562926-Amino-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 576564066-Bromomethyl-2-cyclohexyl-benzothiazole

Product 1

HCID 866296347-chloro-6-[(2-cyclohexyl-benzothiazol-6-yl-methyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Using a method similar to the General Procedure 5-4, combine 6-amino-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (60 mg, 0.21 mmol), 6-bromomethyl-2-cyclohexyl-benzothiazole (0.1 g, 0.31 mmol), potassium carbonate (58 mg, 0.42 mmol) and anhydrous toluene (2 mL) in a sealed tube and heat at 100° C. for 72 h to obtain 7-chloro-6-[(2-cyclohexyl-benzothiazol-6-yl-methyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a colorless oil.

Sources & evidence

ORD record
ord-1e89a0c893d64ed4804a5d8c62e6a34c
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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