Triethylamine → HCID 58504501, compound

HRID 2367333Notes

Reaction equation

HRID 2367333 reaction equation
C(N(CC)CC)C.[CH:8]1([S:14](Cl)(=[O:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[NH2:18][C:19]1[N:24]=[C:23]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([F:33])[CH:26]=2)[CH:22]=[C:21]([N:34]2[C@H:39]([CH3:40])[CH2:38][O:37][C@H:36]([CH2:41][NH2:42])[CH2:35]2)[N:20]=1>C1COCC1>[NH2:18][C:19]1[N:20]=[C:21]([N:34]2[C@H:39]([CH3:40])[CH2:38][O:37][C@H:36]([CH2:41][NH:42][S:14]([CH:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)(=[O:16])=[O:15])[CH2:35]2)[CH:22]=[C:23]([C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([F:33])[CH:26]=2)[N:24]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 237554Cyclohexanesulfonyl chloride2×HCID 58504808HCID 58504808, compound

Product 1

HCID 58504501HCID 58504501, compoundYield 147.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (41 μL, 0.30 mmol) and cylcohexanesulfonyl chloride (44 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 (85 mg, 0.25 mmol) in THF (3 mL), and the mixture was stirred at room temperature under nitrogen for 22 hours. LC-MS indicated only about 25% conversion, so more triethylamine (0.15 mL, 1.08 mmol) and cyclohexanesulfonyl chloride (0.15 mL, 1.03 mmol) were added, and stirring continued at room temperature for another 26 hours. The mixture was then quenched with saturated aqueous NaHCO3 (25 mL) and extracted with EtOAc (3×15 mL). The extracts were washed with brine (15 mL), dried (Na2SO4), filtered, and concentrated in vacuo to give the crude title compound (180 mg, about 45% pure according to LC-MS) as a yellow foam. LC-MS (ES) m/z=489 [M+H]+.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitcontinued at room temperature for another 26 hours
  4. customThe mixture was then quenched with saturated aqueous NaHCO3 (25 mL)
  5. extractionextracted with EtOAc (3×15 mL)
  6. washThe extracts were washed with brine (15 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fcd037fb7424f68bd3a51a07110ab9b
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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