Isopropenyl chloroformate → HCID 131730625, compound

HRID 1257278Notes

Reaction equation

HRID 1257278 reaction equation
[NH2:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([Cl:22])=[C:6]([C:8]2[C:9](=[O:21])[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([Cl:18])[CH:12]=3)[CH:7]=1.C([O-])(O)=O.[Na+].Cl[C:30]([O:32][C:33]([CH3:35])=[CH2:34])=[O:31]>CCOC(C)=O>[Cl:22][C:5]1[C:6]([C:8]2[C:9](=[O:21])[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([Cl:18])[CH:12]=3)=[CH:7][C:2]([NH:1][C:30](=[O:31])[O:32][C:33]([CH3:35])=[CH2:34])=[C:3]([F:23])[CH:4]=1

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 516892Sodium BicarbonateHCID 877715763-(5-Amino-2-chloro-4-fluorophenyl)-7-chloro-1-ethyl-1,6-naphthyridin-2(1h)-one

Product 1

HCID 131730625HCID 131730625, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A bi-phasic mixture of Example A3 (250 mg, 0.710 mmol) in EtOAc (10 mL) and satd. NaHCO3 (15 mL) was treated with isopropenyl chloroformate 9120 mg, 0.984 mmol) and stirred at RT for 2 h. The layers were separated, the organic layer washed with water, then brine, dried over Na2SO4 and concentrated to dryness to afford prop-1-en-2-yl (4-chloro-5-(7-chloro-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)carbamate (292 mg, 94% yield). MS (ESI) m/z: 436.0 [M+H]+.

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with water
  3. dry with materialbrine, dried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-41b2d23eafe7471d9ad1ecf560bb3e99
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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