Benzyl 2-(3-carbamoyl-2-(4-(4-fluorophenoxy)phenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidin-7-yl)phenylcarbamate → 7-(2-Aminophenyl)-2-(4-(4-fluorophenoxy)phenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 64275Notes

Reaction equation

HRID 64275 reaction equation
[C:1]([C:4]1[C:5]([C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)=[N:6][N:7]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[NH:19]C(=O)OCC3C=CC=CC=3)[CH2:11][CH2:10][NH:9][C:8]=12)(=[O:3])[NH2:2]>C(Cl)Cl.CO.[Pd]>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:12]1[N:7]2[N:6]=[C:5]([C:30]3[CH:35]=[CH:34][C:33]([O:36][C:37]4[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=4)=[CH:32][CH:31]=3)[C:4]([C:1]([NH2:2])=[O:3])=[C:8]2[NH:9][CH2:10][CH2:11]1

Participants

5

Reactant 1

HCID 136928057Benzyl 2-(3-carbamoyl-2-(4-(4-fluorophenoxy)phenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidin-7-yl)phenylcarbamate

Product 1

HCID 1369280927-(2-Aminophenyl)-2-(4-(4-fluorophenoxy)phenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carboxamideYield 13.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 2-(3-carbamoyl-2-(4-(4-fluorophenoxyl)phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-7-yl)phenylcarbamate (100 mg, 0.17 mmol) in 5 mL of DCM and 5 mL of CH3OH was added 10% w/w Pd/C (50 mg). After stirring at RT under H2 for 16 hr, the mixture was filtered and the cake was washed with DCM/CH3OH (1/1, 50 mL). The filtrate was concentrated and purified by chromatography column on silica gel eluting with DCM/CH3OH to afford 10 mg (13%) of 7-(2-aminophenyl)-2-(4-(4-fluorophenoxyl)phenyl)-4,5,6,7-tetrahydro pyrazolo[1,5-a]pyrimidine-3-carboxamide as a white solid. 1H NMR (400 MHz, CD3OD-d4) δ 7.39 (d, J=8.8 Hz, 2H), 7.02-6.91 (m, 7H), 6.66 (d, J=7.6 Hz, 1H), 6.53 (t, J=7.6 Hz, 1H), 6.33 (d, J=7.6 Hz, 1H), 5.54-5.50 (m, 1H), 3.30-3.24 (m, 1H), 3.12-3.06 (m, 1H) and 2.31-2.20 (m, 2H). MS (ESI) m/e [M+1]+ 443.9.

Workup

  1. filtrationthe mixture was filtered
  2. washthe cake was washed with DCM/CH3OH (1/1, 50 mL)
  3. concentrationThe filtrate was concentrated
  4. custompurified by chromatography column on silica gel eluting with DCM/CH3OH

Sources & evidence

ORD record
ord-d27dcaeb33f34a1e8b8cbb0f36b8bff6
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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