HCID 136928127, compound → 2'-(4-Phenoxyphenyl)-5',7'-dihydro-4'H-spiro[azetidine-3,6'-pyrazolo[1,5-a]pyrimidine]-3'-carboxamide

HRID 64371Notes

Reaction equation

HRID 64371 reaction equation
C([N:8]1[CH2:35][C:10]2([CH2:15][N:14]3[N:16]=[C:17]([C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:24][CH:23]=4)[C:18]([C:19]([NH2:21])=[O:20])=[C:13]3[NH:12][CH2:11]2)[CH2:9]1)C1C=CC=CC=1>C(Cl)Cl.CO.[Pd]>[O:28]([C:25]1[CH:24]=[CH:23][C:22]([C:17]2[C:18]([C:19]([NH2:21])=[O:20])=[C:13]3[NH:12][CH2:11][C:10]4([CH2:9][NH:8][CH2:35]4)[CH2:15][N:14]3[N:16]=2)=[CH:27][CH:26]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 1

HCID 136928127HCID 136928127, compound

Product 1

HCID 1369281032'-(4-Phenoxyphenyl)-5',7'-dihydro-4'H-spiro[azetidine-3,6'-pyrazolo[1,5-a]pyrimidine]-3'-carboxamideYield 19%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-2′-(4-phenoxyphenyl)-5′,7′-dihydro-4′H-spiro[azetidine-3,6′-pyrazolo[1,5-a]pyrimidine]-3′-carboxamide (200 mg, 0.43 mmol) in 10 mL of DCM and 10 mL of CH3OH was added 10% w/w Pd/C (100 mg). After stirring at RT under H2 for 16 hr, the mixture was filtered and concentrated. The residue was purified by pre-HPLC eluting from 25% to 90% CH3CN in 0.1% TFA in H2O. Fractions containing the desired product were combined and lyophilized overnight to afford 30 mg (19%) of desired product as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.94 (br s, 1H), 8.84 (br s, 1H), 7.50 (d, J=8.4 Hz, 2H), 7.46-7.38 (m, 2H), 7.18 (t, J=8.0 Hz, 1H), 7.08 (d, J=8.0 Hz, 2H), 7.05 (d, J=8.4 Hz, 2H), 6.81 (br s, 1 H), 4.23 (s, 2 H), 3.90-4.00 (m, 2 H), 3.78-3.87 (m, 2 H) and 3.47 (s, 2H). MS (ESI) m/e [M+1]+ 375.9.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified
  4. washby pre-HPLC eluting from 25% to 90% CH3CN in 0.1% TFA in H2O
  5. additionFractions containing the desired product
  6. waitlyophilized overnight

Sources & evidence

ORD record
ord-f94b13f592cd4d4885161c37923a4a58
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

Loading…