Dimethylformamide dimethyl acetal → N'-(9-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)-N,N-dimethylformamidine hydrochloride

HRID 1912812Notes

Reaction equation

HRID 1912812 reaction equation
Cl.[NH2:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:23]=2)=[O:20])=[CH:14][CH:13]=1.CO[CH:35](OC)[N:36]([CH3:38])[CH3:37]>N1C=CC=CC=1>[ClH:28].[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:19](=[O:20])[NH:18][C:15]2[CH:14]=[CH:13][C:12]([N:7]3[CH:6]=[N:5][C:4]4[C:8]3=[N:9][CH:10]=[N:11][C:3]=4[N:2]=[CH:35][N:36]([CH3:38])[CH3:37])=[CH:17][CH:16]=2)=[CH:23][C:24]=1[C:29]([F:31])([F:32])[F:30]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 231551201-[4-(6-Aminopurin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea hydrochloride

Product 1

HCID 69315438N'-(9-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)-N,N-dimethylformamidine hydrochlorideYield 224.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 10 mL of pyridine, 463 mg (0.957 mmol) of 1-[4-(6-amino-purin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea hydrochloride was dissolved, and 455 mg (3.83 mmol) of dimethylformamide dimethylacetal was added thereto and the mixture solution was stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure, and then the residue was triturated with ethyl acetate and collected by filtration, and vacuum dried. The white solid was dissolved in 10 mL of methanol and 4N hydrochloric acid and concentrated under reduced pressure. The residue was triturated with ethyl acetate, collected by filtration, and then vacuum dried to obtain 580 mg (quantitative) of N′-(9-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-yl)-N,N-dimethylformamidine hydrochloride (Table 1, Compound No. 95) as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was triturated with ethyl acetate
  3. filtrationcollected by filtration, and vacuum
  4. customdried
  5. dissolutionThe white solid was dissolved in 10 mL of methanol
  6. concentration4N hydrochloric acid and concentrated under reduced pressure
  7. customThe residue was triturated with ethyl acetate
  8. filtrationcollected by filtration
  9. customvacuum dried

Sources & evidence

ORD record
ord-0488f7499d2446ceb36d14597d03db04
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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