Diisopropylethylamine → Ethylbis(propan-2-yl)amine hydrochloride

HRID 923982Notes

Reaction equation

HRID 923982 reaction equation
[Br:1][C:2]1[C:3]([Cl:22])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH3:23][N:24]1[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.[CH3:31][CH2:32][N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35]>CC(O)C>[Br:1][C:2]1[C:3]([N:27]2[CH2:28][CH2:29][CH2:30][N:24]([CH3:23])[CH2:25][CH2:26]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH3:31][CH2:32][N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35].[ClH:22]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 2

HCID 10997398Ethylbis(propan-2-yl)amine hydrochlorideHCID 899068165-bromo-6-(4-methyl-1,4-diazepan-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.2, 198 mg, 0.50 mmol), 1-methyl-1,4-diazepane (68.6 mg, 0.60 mmol), iPrOH (2 mL) and DIPEA (0.171 mL, 0.129 g, 2.0 mmol) were subjected to MW irradiation at 140° C. for 95 min. The RM was concentrated under reduced pressure to afford the title compound in an equimolar mixture with DIPEA hydrochloride. UPLC-MS (Condition 8) tR=1.2 min, m/z=473.1 [M+H]+, m/z=471.1 [M−H]−.

Workup

  1. customwere subjected to MW irradiation at 140° C. for 95 min
  2. concentrationThe RM was concentrated under reduced pressure

Sources & evidence

ORD record
ord-178791d9f53849039e85f894f3289e02
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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