Isopropenyl chloroformate → HCID 131730623, compound

HRID 1430548Notes

Reaction equation

HRID 1430548 reaction equation
[NH2:1][C:2]1[C:3]([F:24])=[CH:4][C:5]([F:23])=[C:6]([C:8]2[C:9](=[O:22])[N:10]([CH2:20][CH3:21])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH3:19])[CH:12]=3)[CH:7]=1.C([O-])(O)=O.[Na+].Cl[C:31]([O:33][C:34]([CH3:36])=[CH2:35])=[O:32]>CCOC(C)=O>[CH2:20]([N:10]1[C:11]2[C:16](=[CH:15][N:14]=[C:13]([NH:18][CH3:19])[CH:12]=2)[CH:17]=[C:8]([C:6]2[C:5]([F:23])=[CH:4][C:3]([F:24])=[C:2]([NH:1][C:31](=[O:32])[O:33][C:34]([CH3:36])=[CH2:35])[CH:7]=2)[C:9]1=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 516892Sodium BicarbonateHCID 89606312HCID 89606312, compound

Product 1

HCID 131730623HCID 131730623, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of Example A8 (0.078 g, 0.236 mmol) in EtOAc (1.5 mL) was treated with satd. NaHCO3 (1.5 mL) followed by isopropenyl chloroformate (0.036 mL, 0.331 mmol) and the bi-phasic mixture stirred vigorously at RT overnight. The layers were separated, the organic layer washed with brine, dried over MgSO4 and concentrated to dryness to afford prop-1-en-2-yl (5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)carbamate (86 mg, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.64 (s, 1H), 8.41 (s, 1H), 7.83 (s, 1H), 7.61 (s, 1H), 7.36 (t, J=10.2 Hz, 1H), 7.06 (m, 1H), 6.23 (s, 1H), 4.71 (d, J=7.9 Hz, 2H), 4.13 (q, J=7.1 Hz, 2H), 2.85 (d, J=4.9 Hz, 3H), 1.91 (s, 3H), 1.20 (t, J=7.1 Hz, 3H); MS (ESI) m/z: 415.1 [M+H]+.

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-02e62db2f4684d9ba12fb84c96e24d6b
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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