7-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 6-[3-(3-tert-butyl-2-oxo-imidazolidin-1-yl)-prop-1-ynyl]-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 911567Notes

Reaction equation

HRID 911567 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.[C:27]([N:31]1[CH2:35][CH2:34][N:33]([CH2:36][C:37]#[CH:38])[C:32]1=[O:39])([CH3:30])([CH3:29])[CH3:28]>>[C:27]([N:31]1[CH2:35][CH2:34][N:33]([CH2:36][C:37]#[C:38][C:3]2[C:4]3[CH2:10][CH2:9][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:7][CH2:6][C:5]=3[CH:17]=[CH:18][C:2]=2[Cl:1])[C:32]1=[O:39])([CH3:30])([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepineHCID 576559151-tert-Butyl-3-prop-2-ynyl-imidazolidin-2-one

Product 1

HCID 866296646-[3-(3-tert-butyl-2-oxo-imidazolidin-1-yl)-prop-1-ynyl]-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 83.4%

Procedure

Use a method similar to the General Procedure 3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (425 mg, 1 mmol) with 1-tert-butyl-3-prop-2-ynyl-imidazolidin-2-one (360 mg, 2 mmol). Purify by chromatography on silica gel eluting with isohexane/EtOAc (19:1 to 3:2 gradient) to give 6-[3-(3-tert-butyl-2-oxo-imidazolidin-1-yl)-prop-1-ynyl]-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (380 mg, 83%) as a yellow oil. LC-MS (ES+) m/z: 478 (M+Na)+, 456 (M+H)+, tR=4.43 min.

Workup

  1. customPurify by chromatography on silica gel eluting with isohexane/EtOAc (19:1 to 3:2 gradient)

Sources & evidence

ORD record
ord-ec834a42fa4047d59888f68e6c4b9006
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…