Isopropenyl chloroformate → HCID 89827818, compound

HRID 715147Notes

Reaction equation

HRID 715147 reaction equation
Cl[C:2]([O:4][C:5]([CH3:7])=[CH2:6])=[O:3].[NH2:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:20]3[CH:21]=[CH:22][C:23]([F:36])=[C:24]([NH:26][C:27]([NH:29][CH2:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:28])[CH:25]=3)[C:15]([CH3:19])=[N:16]2)=[CH:11][N:10]=1>N1C=CC=CC=1>[CH2:6]=[C:5]([O:4][C:2](=[O:3])[NH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:20]3[CH:21]=[CH:22][C:23]([F:36])=[C:24]([NH:26][C:27]([NH:29][CH2:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:28])[CH:25]=3)[C:15]([CH3:19])=[N:16]2)=[CH:11][N:10]=1)[CH3:7]

Participants

4

Reactant 2

HCID 93846Isopropenyl chloroformateHCID 71735900HCID 71735900, compound

Product 1

HCID 89827818HCID 89827818, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add isopropenyl chloroformate (0.193 mL, 1.769 mmol) to a 0° C. solution of 1-(5-(7-amino-2-methyl-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3,3-dimethylbutyl)urea (0.636 g, 1.608 mmol) in pyridine (10 mL) and stir the mixture for 1 h as it warms to RT. Add water, extract with DCM (3×), dry the combined organics over MgSO4 and concentrate to dryness to afford the title compound (585 mg, 76%). MS(ESI) m/z: 480.2 (M+H+).

Workup

  1. customwarms to RT
  2. extractionAdd water, extract with DCM (3×)
  3. dry with materialdry the combined organics over MgSO4
  4. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-58744ea2e0a645a58304566966c66ebf
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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