Triethylamine → HCID 58504662, compound

HRID 2367329Notes

Reaction equation

HRID 2367329 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[NH2:15][C:16]1[N:21]=[C:20]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([F:30])[CH:23]=2)[CH:19]=[C:18]([N:31]2[C@H:36]([CH3:37])[CH2:35][O:34][C@H:33]([CH2:38][NH2:39])[CH2:32]2)[N:17]=1>C1COCC1>[NH2:15][C:16]1[N:17]=[C:18]([N:31]2[C@H:36]([CH3:37])[CH2:35][O:34][C@H:33]([CH2:38][NH:39][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:32]2)[CH:19]=[C:20]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([F:30])[CH:23]=2)[N:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 58504808HCID 58504808, compound

Product 1

HCID 58504662HCID 58504662, compoundYield 124.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.05 mL, 0.36 mmol) and pivaloyl chloride (0.04 mL, 0.33 mmol) were added to a solution of 4-{2-amino-6-[(2R,5R)-2-(aminomethyl)-5-methyl-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (99 mg, 0.29 mmol) in THF (5 mL), and the mixture was stirred at room temperature under nitrogen for 45 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 as a yellow foam (154 mg, about 75% pure). LC-MS (ES) m/z=427 [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-5ed949e16dd242faa7287846dc1eff98
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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