Benzoyl chloride → HCID 19597444, compound

HRID 611520Notes

Reaction equation

HRID 611520 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[C:12]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=3)=[CH:18][N:17]([CH:27]([CH3:29])[CH3:28])[C:13]=2[N:14]=[CH:15][N:16]=1.C(N(CC)CC)C>ClCCl>[NH2:10][C:11]1[C:12]2[C:19]([C:20]3[CH:21]=[CH:22][C:23]([NH:26][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:24][CH:25]=3)=[CH:18][N:17]([CH:27]([CH3:29])[CH3:28])[C:13]=2[N:14]=[CH:15][N:16]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 19597418HCID 19597418, compound

Product 1

HCID 19597444HCID 19597444, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Benzoyl chloride (101 mg) in dichloromethane (1.0 ml) was added to a mixture of 4-amino-5-(4-aminophenyl)-7-isopropylpyrrolo[2,3-d]pyrimidine (175 mg), in dichloromethane (7 ml) and triethylamine (73 mg) at 0° C. under nitrogen with stirring. The mixture was stirred at 0° C. for four hours and then allowed to warm up to ambient temperature over one hour. The reaction mixture was stirred at ambient temperature for 18 hours and then quenched by the addition of saturated sodium bicarbonate solution (10 ml) with ice-cooling. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×20 ml). The combined organic layers were washed with water, dried and evaporated to give a pale yellow solid which was purified by preparative HPLC to give N-(4-{4-amino-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl}phenyl)-benzamide, m.p. 192-195° C.

Workup

  1. temperatureto warm up to ambient temperature over one hour
  2. stirringThe reaction mixture was stirred at ambient temperature for 18 hours
  3. customquenched by the addition of saturated sodium bicarbonate solution (10 ml) with ice-
  4. temperaturecooling
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (3×20 ml)
  7. washThe combined organic layers were washed with water
  8. customdried
  9. customevaporated
  10. customto give a pale yellow solid which
  11. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-212deeadf2054a3387184f6a4922aa64
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

Loading…