Acetic Acid → HCID 19610585, compound

HRID 1602233Notes

Reaction equation

HRID 1602233 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])=O.[NH2:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[N:19][C:20]=2[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[NH:15][N:14]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO.CN1C(=O)N(C)CC1>[C:6]([C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH2:1][NH:12][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[N:19][C:20]=2[NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[NH:15][N:14]=1)([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 120773-CarboxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178509242HCID 178509242, compound

Product 1

HCID 19610585HCID 19610585, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

225 mg (1.50 mmol) of 3-formyl-benzoic acid are added to a solution of 261 mg (1.00 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine in 26 ml of methanol, 13 ml of DMEU and 120 mg (2.0 mmol) of acetic acid under a N2 atmosphere. The reaction mixture is stirred for 1 hour, during which time a solid precipitates, and then 440 mg (7.0 mmol) of NaCNBH3 are added. Stirring is carried out for 5 days, the suspension changing to a clear solution. The methanol is evaporated off using a rotary evaporator. The residue is poured into 0.6 liter of water and stirred for 3 hours to complete the reaction. Filtering with suction, washing with water and diethyl ether, stirring in hot ethanol, cooling and filtering yield 3-(3-carboxy-benzylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (3-{[4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl-amino]methyl}-benzoic acid); m.p. 294-296° C.; HPLC: TRet (Grad5-40)=20.1; FAB-MS: (M+H)+ =395.

Workup

  1. customprecipitates
  2. stirringStirring
  3. waitis carried out for 5 days
  4. customThe methanol is evaporated off
  5. customa rotary evaporator
  6. additionThe residue is poured into 0.6 liter of water
  7. stirringstirred for 3 hours
  8. customthe reaction
  9. filtrationFiltering with suction
  10. washwashing with water and diethyl ether
  11. stirringstirring in hot ethanol
  12. temperaturecooling
  13. filtrationfiltering

Sources & evidence

ORD record
ord-8c94ebe340264647a5ae9b9c5e241037
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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