3-Amino-1-propanol → Ethylbis(propan-2-yl)amine hydrochloride

HRID 924003Notes

Reaction equation

HRID 924003 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].[NH2:23][CH2:24][CH2:25][CH2:26][OH:27].[CH3:28][CH2:29][N:30]([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32]>CC(O)C>[Br:1][C:2]1[C:3]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])=[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].[CH3:28][CH2:29][N:30]([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32].[ClH:22]

Participants

6

Reactant 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 2

HCID 10997398Ethylbis(propan-2-yl)amine hydrochlorideHCID 899067795-bromo-6-((3-hydroxypropyl)amino)-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), 3-aminopropan-1-ol (45 mg, 0.60 mmol), iPrOH (2 mL) and DIPEA (0.171 mL, 0.129 g, 1.0 mmol) were subjected to MW irradiation at 140° C. for 150 min. The vial was cooled to RT and the RM was evaporated to dryness under reduced pressure. No further purification was required to afford the title compound as an equimolar mixture with DIPEA hydrochloride. UPLC-MS (Condition 8) tR=1.46 min, m/z=434.0 [M+H]+, m/z=432.1 [M−H]−.

Workup

  1. customwere subjected to MW irradiation at 140° C. for 150 min
  2. customthe RM was evaporated to dryness under reduced pressure
  3. customNo further purification

Sources & evidence

ORD record
ord-2e2065cb160b4fd39ba24d8342d28327
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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