Dimethylamine → HCID 178484929, compound

HRID 1912811Notes

Reaction equation

HRID 1912811 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[C:26]4[CH:25]=[CH:24][N:23]=[C:22]([C:27]#[N:28])[C:21]=4[N:20]=[CH:19]3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].C[O-].[Na+].[CH3:36][NH:37]C>CO.C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[NH:11][C:12]2[CH:13]=[CH:14][C:15]([N:18]3[C:26]4[CH:25]=[CH:24][N:23]=[C:22]([C:27]([NH:37][CH3:36])=[NH:28])[C:21]=4[N:20]=[CH:19]3)=[CH:16][CH:17]=2)=[CH:4][C:3]=1[C:29]([F:30])([F:31])[F:32]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 10942334Sodium MethoxideHCID 23154975HCID 23154975, compound

Product 1

HCID 178484929HCID 178484929, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent2×

Procedure

In 5 mL of methanol, 12 mg (0.026 mmol) of 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-[4-(4-cyanoimidazo-[4,5-c]pyridin-1-yl)phenyl]urea prepared in Example 91 was dissolved, and one drop (a catalytic amount) of a 28% methanol solution of sodium methylate was added thereto and the solution was stirred at room temperature for six hours. The reaction solution was neutralized with one drop of acetic acid, and then 50 μL of a dimethylamine 40% methanol solution was added thereto and the mixture solution was further stirred at room temperature for 14 hours. The solvent was distilled under reduced pressure, and the residue was separated by reversed phase high-pressure liquid chromatography (C18 Column, acetonitrile:water=55:45, 0.05% trifluoroacetic acid). The fraction containing a target product was concentrated, and then trifluoroacetic acid was replaced with hydrochloric acid to obtain 4.2 mg (30%) of 1-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-N-methyl-1H-imidazo[4,5-c]pyridine-4-carboxamidine hydrochloride (Table 1, Compound No. 94) as a white solid.

Workup

  1. stirringthe mixture solution was further stirred at room temperature for 14 hours
  2. distillationThe solvent was distilled under reduced pressure
  3. customthe residue was separated by reversed phase high-pressure liquid chromatography (C18 Column, acetonitrile:water=55:45, 0.05% trifluoroacetic acid)
  4. additionThe fraction containing a target product
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-7c9bee3829d14a4bafdc9fd0047287ea
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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