7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → HCID 86624163, compound

HRID 1191116Notes

Reaction equation

HRID 1191116 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1OS(C(F)(F)F)(=O)=O.[NH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][S:36][CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:31][N:30]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][S:36][CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[CH:31][N:30]=1

Participants

4

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 58495532HCID 58495532, compound

Product 1

HCID 86624163HCID 86624163, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Use a method similar to the General Procedure 1-2 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (245 mg, 0.58 mmol) with 2-aminomethyl-5-cyclopentylthiomethyl-pyridine (230 mg, 1 mmol) in toluene (5 mL). Purify the crude mixture by chromatography on silica gel eluting with hexane/THF (49:1 to 7:3 gradient) to obtain 7-chloro-6-[(5-cyclopentylthiomethyl-pyridin-2-ylmethyl)-amino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (170 mg, 59%). MS (ES+) m/z: 498.1 (M+H)+.

Workup

  1. customPurify the crude mixture by chromatography on silica gel eluting with hexane/THF (49:1 to 7:3 gradient)

Sources & evidence

ORD record
ord-11de5c2c17da4a4d8e3e16c82dad2071
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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