Benzhydrylamine → HCID 178522801, compound

HRID 574655Notes

Reaction equation

HRID 574655 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[N:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[C:28]1([CH:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[NH2:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CCN(CC)CC>CN(C=O)C.O>[CH:34]([NH:35][C:8]([C:7]1[C:2]([OH:1])=[N:3][C:4]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)=[N:5][CH:6]=1)=[O:10])([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178524762HCID 178524762, compound

Product 1

HCID 178522801HCID 178522801, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

4-Hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid (1-1-a, 8 g, 38.8 mmol) and CDI (7.24 g, 44.6 mmol) was dissolved in DMF (80 mL), stirred for 45 min at 105° C., then cooled to 77° C. Diphenylmethanamine (9.2 g, 50.4 mmol) and Et3N (5.41 ml, 38.8 mmol) were then added to the solution at 77° C. and the reaction mixture was stirred for 5 h. The resulting mixture was cooled to ambient temperature, diluted with 150 ml of water, extracted with ethyl acetate (3 times 150 ml). The organic phases were combined, washed with brine, dried over anhydrous Na2SO4, purified by recrystillized in EtOH/Et2O (1/10). A yellow solid was obtained as product, 1-1-b, (6.4 g, 45%). 1H NMR (300 MHz, DMSO-d6) δ 6.32-6.34 (d, J=8.4, 1H), 6.50-6.51 (m, 1H), 7.29-7.43 (m, 11H), 7.74 (s, 1H), 8.55-8.58 (m, 2H), 11.77 (s, 1H). LC-MS 372 [MH]+.

Workup

  1. temperaturecooled to 77° C
  2. stirringthe reaction mixture was stirred for 5 h
  3. temperatureThe resulting mixture was cooled to ambient temperature
  4. extractionextracted with ethyl acetate (3 times 150 ml)
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. custompurified
  8. customA yellow solid was obtained as product

Sources & evidence

ORD record
ord-84a12e12f24d456fac22ed36269f123c
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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