Triethylamine → HCID 58504524, compound

HRID 2367331Notes

Reaction equation

HRID 2367331 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[N:19]=[C:18]([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([F:28])[CH:21]=2)[CH:17]=[C:16]([N:29]2[C@H:34]([CH3:35])[CH2:33][O:32][C@H:31]([CH2:36][NH2:37])[CH2:30]2)[N:15]=1>C1COCC1>[NH2:13][C:14]1[N:15]=[C:16]([N:29]2[C@H:34]([CH3:35])[CH2:33][O:32][C@H:31]([CH2:36][NH:37][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:30]2)[CH:17]=[C:18]([C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([F:28])[CH:21]=2)[N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58504808HCID 58504808, compound

Product 1

HCID 58504524HCID 58504524, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (41 μL, 0.30 mmol) and methanesulfonyl chloride (21 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 30 minutes. The mixture was quenched with saturated aqueous NaHCO3 (10 mL) and extracted with EtOAc (2×10 mL). The extracts were washed with brine (15 mL), dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound (108 mg, about 90% pure) as a yellow solid. LC-MS (ES) m/z=421 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-86c7eafa37644acea790bdd5aa93b0a5
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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