Gamma-Butyrolactone → HCID 178520698, compound

HRID 1068954Notes

Reaction equation

HRID 1068954 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[NH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[C:27]1(=[O:32])[O:31][CH2:30][CH2:29][CH2:28]1>CN(C)C1C=CN=CC=1.CO>[Cl:26][C:22]1[CH:21]=[C:20]([NH:19][C:17]2[N:16]=[CH:15][N:14]=[C:13]3[NH:12][N:11]=[C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][NH:1][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][OH:32])[CH:4]=4)[C:18]=23)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 7302Gamma-Butyrolactone2×HCID 178509838HCID 178509838, compound

Product 1

HCID 178520698HCID 178520698, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 300 mg (0.8054 mmol) of 3-(3-aminomethyl-phenylamino)4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (water content: 1.79%; see Step 90.5), 277 mg (3.22 mmol) of -γ-butyrolactone, 2 mg of 4-dimethylamino-pyridine and 5 ml of methanol is stirred for 10 hours at 95° C. and, after a further addition of 277 mg (3.22 mmol) of γ-butyrolactone and 4 mg of 4-dimethylaminopyridine, for a further 16 hours at 100° C. The reaction mixture is then concentrated by evaporation in vacuo, and the residue is stirred with ethyl acetate and filtered, and the filter residue is recrystallized from methanol, yielding 4-(3-chloro-phenylamino)-3-[3-({4-hydroxy-butyryl-amino}-methyl)-phenylamino]-1H-pyrazolo[3,4-d]pyrimidine having a water content of 0.67%; m.p. 182-184° C.

Workup

  1. waitfor a further 16 hours at 100° C
  2. concentrationThe reaction mixture is then concentrated by evaporation in vacuo
  3. stirringthe residue is stirred with ethyl acetate
  4. filtrationfiltered
  5. customthe filter residue is recrystallized from methanol

Sources & evidence

ORD record
ord-58f6ad91f33a4bb397c94d269238b855
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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