Benzenamine, 3-chloro-, hydrochloride (1:1) → 3-[2-(Boc-amino)-ethylamino]-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1068956Notes

Reaction equation

HRID 1068956 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[C:16]([C:17]#[N:18])=[C:15]([N:19]([CH3:21])C)[N:14](N=C)[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[Cl:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29]>CO>[C:4]([O:3][C:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[C:16]2[C:15](=[N:19][CH:21]=[N:18][C:17]=2[NH:29][C:28]2[CH:30]=[CH:31][CH:32]=[C:26]([Cl:25])[CH:27]=2)[NH:14][N:13]=1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 696975253-[2-(Boc-amino)-ethylamino]-4-cyano-5-dimethylamino-methyleneamino-pyrazole

Product 1

HCID 211906093-[2-(Boc-amino)-ethylamino]-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 35 g (108.9 mmol) of 3-[2-(Boc-amino)-ethylamino]-4-cyano-5-dimethylamino-methyleneamino-pyrazole, 17.9 g (109.1 mmol) of 3-chloro-aniline hydrochloride and 350 ml of methanol is heated under reflux for 30 hours and then stirred at RT for 15 hours. Filtration and washing the filter residue with methanol yield 3-[2-(tert-butyloxy-carbonyl-amino)-ethylamino]-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine having a water content of 2.39%; m.p. 206-208° C.; ESI-MS: (M−H)−=402.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 30 hours
  3. filtrationFiltration
  4. washwashing the filter residue with methanol

Sources & evidence

ORD record
ord-42c25ec23f3a40fdb1defd6213fbaf90
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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