7-chloro-6-[4-(2,2-dimethyl-propionylamino)-but-1-ynyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 7-Chloro-6-[4-(2,2-dimethyl-propionylamino)-but-1-ynyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1965980Notes

Reaction equation

HRID 1965980 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][N:8](C(=O)C(F)(F)F)[CH2:9][CH2:10][C:4]=2[C:3]=1[C:19]#[C:20][CH2:21][CH2:22][NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>N.CO.O.C1COCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:19]#[C:20][CH2:21][CH2:22][NH:23][C:24](=[O:29])[C:25]([CH3:27])([CH3:26])[CH3:28]

Participants

4

Reactant 1

HCID 866227837-chloro-6-[4-(2,2-dimethyl-propionylamino)-but-1-ynyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 597874217-Chloro-6-[4-(2,2-dimethyl-propionylamino)-but-1-ynyl]-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 94.4%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Use a method similar to the General Procedure 1-1, using 7N ammonia in methanol/water/THF (10:1:1 ratio) as solvent, to deprotect 7-chloro-6-[4-(2,2-dimethyl-propionylamino)-but-1-ynyl]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (62 mg, 0.14 mmol) and afford the title compound as an oil (44 mg, 91%). MS (ES+) m/z: 333.1 (M+H)+.

Sources & evidence

ORD record
ord-ec0b1b9b4dea412498e32a0df7d1fe33
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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