Dimethylamine → 1-[3,5-dichloro-4-(3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b: 4',3'-f]azepin-2-yl)phenyl]-N,N-dimethylmethanamine

HRID 1043479Notes

Reaction equation

HRID 1043479 reaction equation
[CH3:1][NH:2][CH3:3].[H-].[Na+].[Cl:6][C:7]1[CH:12]=[C:11]([CH2:13]Cl)[CH:10]=[C:9]([Cl:15])[C:8]=1[C:16]1[NH:17][C:18]2[C:24]3[CH:25]=[CH:26][N:27]=[CH:28][C:23]=3[NH:22][C:21]3[N:29]=[CH:30][CH:31]=[CH:32][C:20]=3[C:19]=2[N:33]=1>CN(C)C=O.CO>[Cl:6][C:7]1[CH:12]=[C:11]([CH2:13][N:2]([CH3:3])[CH3:1])[CH:10]=[C:9]([Cl:15])[C:8]=1[C:16]1[NH:17][C:18]2[C:24]3[CH:25]=[CH:26][N:27]=[CH:28][C:23]=3[NH:22][C:21]3[N:29]=[CH:30][CH:31]=[CH:32][C:20]=3[C:19]=2[N:33]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 24758Sodium hydrideHCID 66887168HCID 66887168, compound

Product 1

HCID 160720251-[3,5-dichloro-4-(3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b: 4',3'-f]azepin-2-yl)phenyl]-N,N-dimethylmethanamineYield 31%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of dimethylamine (23 μL, 2.0 M in tetrahydrofuran) was dissolved in N,N-dimethylformamide (0.5 mL) and cooled to 0° C. Sodium hydride (1.1 mg, 0.05 mmol) was added and the mixture was stirred for 15 minutes. 2-[2,6-dichloro-4-(chloromethyl)phenyl]-3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4′,3′-f]azepine (10.0 mg, 0.02 mmol) was added and the mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with methanol and purified on preparative LCMS at pH 10 to give the desired product (3.2 mg, 31%). LC/MS: 437 (M+H)+.

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. custompurified on preparative LCMS at pH 10

Sources & evidence

ORD record
ord-81810d57a7544dff82b1d3f3c16505c8
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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