Benzenamine, 3-chloro-, hydrochloride (1:1) → HCID 178452690, compound

HRID 1602251Notes

Reaction equation

HRID 1602251 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[C:10]([O:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:28](C#N)=[C:27]([N:31]=[CH:32][N:33]([CH3:35])C)[NH:26][N:25]=2)=[CH:20][CH:19]=1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CO>[C:10]([O:14][C:15]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[C:28]3[C:27](=[N:31][CH:32]=[N:33][C:35]=3[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[C:3]([Cl:2])[CH:4]=3)[NH:26][N:25]=2)=[CH:22][CH:23]=1)=[O:16])([CH3:11])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 178484263HCID 178484263, compound

Product 1

HCID 178452690HCID 178452690, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With the exclusion of air, 172 mg (1.05 mmol) of 3-chloro-aniline hydrochloride (see Step 14.4) are added to 248 mg (0.70 mmol) of N'-[3-(4-tert-butoxycarbonylamino-phenyl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethylformamidine in 2 ml of methanol and the reaction mixture is boiled for 19 hours. The reaction mixture is then concentrated by evaporation and chromatographed (SiO2, methylene chloride/ethanol [20:1]). Stirring with diethyl ether/hexane yields 3-(4-tert-butoxycarbonylamino-phenyl)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine; m.p. 165-168° C. (decomposition); FAB-MS: (M)+= 436; HPLC: TRet (Grad20-100)=15.4.

Workup

  1. concentrationThe reaction mixture is then concentrated by evaporation
  2. customchromatographed (SiO2, methylene chloride/ethanol [20:1])

Sources & evidence

ORD record
ord-b8cfb2af3c96492cb891c292fbf50d94
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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