(5-Fluoropyridin-2-yl)methanamine → 7-chloro-6-[(5-fluoro-pyridin-2-ylmethyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 911400Notes

Reaction equation

HRID 911400 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][N:4]=1.[Cl:10][C:11]1[CH:27]=[CH:26][C:14]2[CH2:15][CH2:16][N:17]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:18][CH2:19][C:13]=2[C:12]=1OS(C(F)(F)F)(=O)=O>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:27]=[CH:26][C:14]2[CH2:15][CH2:16][N:17]([C:20](=[O:25])[C:21]([F:22])([F:24])[F:23])[CH2:18][CH2:19][C:13]=2[C:12]=1[NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 45079543(5-Fluoropyridin-2-yl)methanamineHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 866296387-chloro-6-[(5-fluoro-pyridin-2-ylmethyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Use a method similar to the General Procedure 5-1 to couple 2-aminomethyl-5-fluoro-pyridine (230 mg, 1.8 mmol) and a solution of 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (500 mg, 1.2 mmol) in toluene (4 mL). Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1 to 1:1) followed by SCX chromatography to give 7-chloro-6-[(5-fluoro-pyridin-2-ylmethyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (302 mg, 64%). GC-MS m/z: 402 (M+).

Workup

  1. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1 to 1:1)

Sources & evidence

ORD record
ord-2b607da947f74608997b4387a6c80160
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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