2-(4-{[7-(benzyloxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(2,3-difluorophenyl)acetamide → N-(2,3-difluorophenyl)-2-{4-[(7-hydroxyquinazolin-4-yl)amino]-1H-pyrazol-1-yl}acetamide

HRID 639966Notes

Reaction equation

HRID 639966 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:21]=[N:22][N:23]([CH2:25][C:26]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=4[F:36])=[O:27])[CH:24]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O>[F:36][C:30]1[C:31]([F:35])=[CH:32][CH:33]=[CH:34][C:29]=1[NH:28][C:26](=[O:27])[CH2:25][N:23]1[CH:24]=[C:20]([NH:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=3)[N:16]=[CH:15][N:14]=2)[CH:21]=[N:22]1

Participants

3

Reactant 1

HCID 686382742-(4-{[7-(benzyloxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(2,3-difluorophenyl)acetamide

Product 1

HCID 135425081N-(2,3-difluorophenyl)-2-{4-[(7-hydroxyquinazolin-4-yl)amino]-1H-pyrazol-1-yl}acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(4-{[7-(benzyloxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)-N-(2,3-difluorophenyl)acetamide (836 mg, 1.60 mmol) was dissolved in trifluoroacetic acid (8 ml) and heated under reflux for 2.5 hours. The solution was concentrated and the residual oil was dissolved in methanol and neutralised with an aqueous solution of sodium bicarbonate. Water was added to the mixture and the solid recovered by filtration and dried in vacuo to yield N-(2,3-difluorophenyl)-2-{4-[(7-hydroxyquinazolin-4-yl)amino]-1H-pyrazol-1-yl}acetamide (633 mg, 100% yield):

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours
  3. concentrationThe solution was concentrated
  4. dissolutionthe residual oil was dissolved in methanol and neutralised with an aqueous solution of sodium bicarbonate
  5. additionWater was added to the mixture
  6. filtrationthe solid recovered by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-c3b8288a9a7548f8883e46f0699629e0
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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