Trifluoroacetic acid → HCID 178418717, compound

HRID 1166259Notes

Reaction equation

HRID 1166259 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[C:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:19]=2)[NH:15][N:16]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[C:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:19]=2)[NH:15][N:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178418708HCID 178418708, compound

Product 1

HCID 178418717HCID 178418717, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [5-(3-tert-butoxycarbonylaminoprop-1-yl)-2H-pyrazol-3-yl]-(2-phenyl-quinazolin-4-yl)-amine (III-80) (250 mg, 0.56 mmol), in dichloromethane (3 mL) at 0° C. was treated with TFA (2 mL). The mixture was warmed to room temperature then concentrated in vacuo. The residue was triturated and concentrated from dichloromethane (3×5 mL) and ether, then triturated with dichloromethane to crystallize the TFA salt. The resulting solid was collected by filtration and dissolved in a mixture of ethanol (3 mL) and water (3 mL). Potassium carbonate was added in portions to achieve pH 8 then the mixture allowed to crystallize. The product was collected by filtration and dried at 80° C. under vacuum to afford III-79 as an off-white powder (122 mg, 63%): mp 205-207° C.; 1H NMR (DMSO) δ 1.68-1.83 (2H, m), 2.65-2.80(4H, m), 6.80 (1H, s), 7.50-7.60 (4H, m), 7.80-7.90 (2H, m), 8.45-8.53 (2H, m), 8.65 (1H, d), 10.45 (1H, br s); IR (solid) 1621, 1598, 1568, 1533, 1484, 1414, 1364, 1327, 1169, 1030, 951, 830, 776, 764, 705, 677; MS 345.3(M+H)+.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was triturated
  3. concentrationconcentrated from dichloromethane (3×5 mL) and ether
  4. customtriturated with dichloromethane
  5. customto crystallize the TFA salt
  6. filtrationThe resulting solid was collected by filtration
  7. dissolutiondissolved in a mixture of ethanol (3 mL) and water (3 mL)
  8. additionPotassium carbonate was added in portions
  9. customto crystallize
  10. filtrationThe product was collected by filtration
  11. customdried at 80° C. under vacuum

Sources & evidence

ORD record
ord-c0463c7358ac4093b934ee1c635bd416
Source dataset
uspto-grants-2003_09
Patent number
US06613776B2

Reaction notes

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