1,3-Propanediamine, N1,N1,N3-trimethyl- → Ethylbis(propan-2-yl)amine hydrochloride

HRID 924012Notes

Reaction equation

HRID 924012 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]([CH3:30])[CH2:25][CH2:26][CH2:27][NH:28][CH3:29].[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:28]([CH2:27][CH2:26][CH2:25][N:24]([CH3:30])[CH3:23])[CH3:29])=[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 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 81531DiisopropylethylamineHCID 867025955-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 2

HCID 10997398Ethylbis(propan-2-yl)amine hydrochlorideHCID 899066305-bromo-6-((3-(dimethylamino)propyl)(methyl)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, 237 mg, 0.60 mmol), N1,N1,N3-trimethylpropane-1,3-diamine (84 mg, 0.72 mmol), iPrOH (2.4 mL) and DIPEA (0.205 mL, 0.155 g, 1.2 mmol) were subjected to MW irradiation at 140° C. for 120 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 in an equimolar mixture with DIPEA hydrochloride. UPLC-MS (Condition 8) tR=2.18 min, m/z=475.1 [M+H]+, m/z=473.1 [M−H]−.

Workup

  1. customwere subjected to MW irradiation at 140° C. for 120 min
  2. customthe RM was evaporated to dryness under reduced pressure
  3. customNo further purification

Sources & evidence

ORD record
ord-fa121dfd44c4483ab87ff62a85a53005
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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