Benzenamine, 3-chloro-, hydrochloride (1:1) → 4-(3-chloro-phenylamino)-3-(4-tert-butyloxycarbonyl-piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1068892

Reaction equation

HRID 1068892 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:18]([C:19]#[N:20])=[C:17]([N:21]=[CH:22][N:23](C)C)[NH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)N>CO>[Cl:27][C:28]1[CH:34]=[C:33]([NH:20][C:19]2[N:23]=[CH:22][N:21]=[C:17]3[NH:16][N:15]=[C:14]([N:11]4[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]4)[C:18]=23)[CH:32]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 54424143N'-[3-(4-tert-butoxycarbonyl-piperazin-1-yl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethyl-formamidine

Product 1

HCID 211906074-(3-chloro-phenylamino)-3-(4-tert-butyloxycarbonyl-piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With the exclusion of air, 16.2 9 (46.6 mmol) of N′-[3-(4-tert-butoxycarbonyl-piperazin-1 -yl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethyl-formamidine in 130 ml methanol are heated to boiling with 11.47 g (70 mmol) of 3-chloro-aniline hydrochloride. After 9 hours the reaction mixture is cooled, filtered and washed with methanol and DIPE. Stirring the crude product in boiling ethanol, cooling and filtration yield 4-(3-chloro-phenylamino)-3-(4-tert-butyloxycarbonyl-piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine; HPLC: tRet(grad20-100/20)=15.7; IR (KBr) interalia 1706 s, 1631 s, 1610 s, 1589 s, 1508 m, 1482 s, 1425 m, 1364 m, 1304 m, 1283 m, 1245 m, 1170 m, 1122 m.

Workup

  1. temperatureAfter 9 hours the reaction mixture is cooled
  2. filtrationfiltered
  3. washwashed with methanol and DIPE
  4. temperaturecooling
  5. filtrationfiltration

Sources & evidence

ORD record
ord-0c6a5e6e8741484384f1f6d5cd40256e
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Linked notes

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