Dimethylamine → HCID 44556132, compound

HRID 221990Notes

Reaction equation

HRID 221990 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]([NH:5][C:6]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][C:24]4[C:23]5=[N:33][N:34]=[C:35]([C:36]6[N:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[N:22]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:13][CH:12]=2)[CH2:9][C:8](=O)[CH2:7]1)=[O:4].[CH3:44][NH:45][CH3:46].CCOC(C)=O.C([O-])(O)=O.[Na+]>CO.[Cl-].[Na+].O>[CH3:44][N:45]([CH3:46])[CH:8]1[CH2:9][C:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:43])[F:42])([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][C:24]4[C:23]5=[N:33][N:34]=[C:35]([C:36]6[N:37]=[CH:38][CH:39]=[CH:40][N:41]=6)[N:22]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:15][CH:16]=2)[CH2:7]1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 582298532,2,2-trifluoro-N-(3-oxo-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide

Product 1

HCID 44556132HCID 44556132, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of 2,2,2-trifluoro-N-(3-oxo-1-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-2) (20 mg, 0.035 mmol) and dimethylamine (2M in THF, 0.052 mL, 0.104 mmol) in MeOH (0.3 mL) was added Zn(BH3CN)2 (0.3M in MeOH, 0.6 mL, 0.18 mmol), and the mixture was stirred at room temperature for overnight. To the mixture was added EtOAc, sat. NaHCO3, and brine. The resulting solid was collected by filtration to give N-(3-(dimethylamino)-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)-2,2,2-trifluoroacetamide (4-4) as colorless solid. HRMS (M+H)+: observed=609.2338, calculated=609.2342.

Workup

  1. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-130f4f9e6be34e76a3618e573133c394
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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