Isopropenyl chloroformate → HCID 89827812, compound

HRID 715136Notes

Reaction equation

HRID 715136 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[C:14]([CH3:21])=[CH:15][C:16]([F:20])=[C:17]([CH:19]=3)[NH2:18])[C:8]([CH3:12])=[N:9]2)=[CH:4][N:3]=1.C([O-])(O)=O.[Na+].Cl[C:28]([O:30][C:31]([CH3:33])=[CH2:32])=[O:29]>CCOC(C)=O>[CH2:32]=[C:31]([O:30][C:28](=[O:29])[NH:18][C:17]1[CH:19]=[C:13]([C:7]2[C:8]([CH3:12])=[N:9][C:10]3[C:5]([CH:6]=2)=[CH:4][N:3]=[C:2]([Cl:1])[CH:11]=3)[C:14]([CH3:21])=[CH:15][C:16]=1[F:20])[CH3:33]

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 516892Sodium BicarbonateHCID 898142035-(7-Chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluoro-4-methylaniline

Product 1

HCID 89827812HCID 89827812, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 5-(7-chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluoro-4-methylaniline (0.5 g, 1.657 mmol) in EtOAc (10 mL) with satd. NaHCO3 (10 mL) followed by isopropenyl chloroformate (0.199 mL, 1.823 mmol) and stir the bi-phasic mixture at RT overnight. Separate the layers, extract the aqueous with EtOAc (2×), dry the combined organics over MgSO4 and concentrate to dryness to the title compound (646 mg, 101%). MS (ESI) m/z: 386.1 (M+H+).

Workup

  1. customSeparate the layers
  2. extractionextract the aqueous with EtOAc (2×)
  3. dry with materialdry the combined organics over MgSO4
  4. concentrationconcentrate to dryness to the title compound (646 mg, 101%)

Sources & evidence

ORD record
ord-482357982caa47678c6d1dcc2c003384
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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