3-Fluorobenzylamine → HCID 86629644, compound

HRID 911408Notes

Reaction equation

[Cl:1][C:2]1[CH:18]=[C:17]([F:19])[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.[F:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32][NH2:33]>>[Cl:1][C:2]1[CH:18]=[C:17]([F:19])[C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:13])([F:15])[F:14])[CH2:9][CH2:10][C:4]=2[C:3]=1[NH:33][CH2:32][C:31]1[CH:34]=[CH:35][CH:36]=[C:29]([F:28])[CH:30]=1

Participants

Reactant 2

HCID 668533-Fluorobenzylamine

HCID 57656341HCID 57656341, compound

Product 1

HCID 86629644HCID 86629644, compoundYield 28%

Procedure

Use a method similar to the General Procedure 5-1 to couple 7-chloro-9-fluoro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (130 mg, 0.3 mmol) with 3-fluorobenzylamine (100 □L, 0.89 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1 and 4:1) followed by SCX chromatography to give 7-chloro-9-fluoro-6-(3-fluorobenzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (35 mg, 28%). MS (ES+) m/z: 401 (M+H)+.

Workup

customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1 and 4:1)

Sources & evidence

ORD record: ord-6e8f6fe0fb5045fa91ceb187d0edf65c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022062B2

Reaction notes

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