Benzoyl chloride → HCID 58504567, compound

HRID 2367325Notes

Reaction equation

HRID 2367325 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:17][C:18]1[N:23]=[C:22]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([F:32])[CH:25]=2)[CH:21]=[C:20]([N:33]2[C@H:38]([CH3:39])[CH2:37][O:36][C@H:35]([CH2:40][NH2:41])[CH2:34]2)[N:19]=1>C1COCC1>[NH2:17][C:18]1[N:19]=[C:20]([N:33]2[C@H:38]([CH3:39])[CH2:37][O:36][C@H:35]([CH2:40][NH:41][C:8](=[O:15])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:34]2)[CH:21]=[C:22]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([F:32])[CH:25]=2)[N:23]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 58504808HCID 58504808, compound

Product 1

HCID 58504567HCID 58504567, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (48 μL, 0.34 mmol) and benzoyl chloride (31 μL, 0.27 mmol) were added to a solution of 4-{2-amino-6-[(2R,5R)-2-(aminomethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (77 mg, 0.23 mmol) in THF (5 mL), and the mixture was stirred at room temperature under nitrogen for 30 minutes. The mixture was quenched with saturated aqueous NaHCO3 (15 mL) and extracted with EtOAc (2×10 mL). The extracts were washed with brine (10 mL), dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound (115 mg) as a yellow glass. LC-MS (ES) m/z=447 [M+H]+.

Workup

  1. customThe mixture was quenched with saturated aqueous NaHCO3 (15 mL)
  2. extractionextracted with EtOAc (2×10 mL)
  3. washThe extracts were washed with brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdf324bb814e4dd79dcb4d7f209f3893
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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