1-[4-(2-Methyl-1,3-dioxolan-2-yl)phenyl]methanamine → HCID 59828873, compound

HRID 1190943Notes

Reaction equation

HRID 1190943 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.[CH3:27][C:28]1([C:33]2[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=2)[O:32][CH2:31][CH2:30][O:29]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:38][CH2:37][C:36]1[CH:35]=[CH:34][C:33]([C:28]2([CH3:27])[O:29][CH2:30][CH2:31][O:32]2)=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 124353861-[4-(2-Methyl-1,3-dioxolan-2-yl)phenyl]methanamineHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 59828873HCID 59828873, compoundYield 68%

Procedure

Use a method similar to the General Procedure 1-3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (200 mg, 0.47 mmol) with 4-(2-methyl-[1,3]dioxolan-2-yl)-benzylamine (prepared by following the procedure described in J. Med. Chem. 1978, 21, 507) (182 mg, 0.94 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 19:1 and 9:1) to obtain the desired intermediate as an oil (150 mg, 68%). GC-MS m/z: 468 (M+).

Workup

  1. customprepared
  2. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 19:1 and 9:1)

Sources & evidence

ORD record
ord-086c59d59f134631a659c2e40eb31c18
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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