Isopropenyl chloroformate → HCID 89815666, compound

HRID 715106Notes

Reaction equation

HRID 715106 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[CH:4][C:5]([F:21])=[C:6]([C:8]2[C:9]([CH3:20])=[N:10][C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH3:19])[CH:12]=3)[CH:7]=1.Cl[C:24]([O:26][C:27]([CH3:29])=[CH2:28])=[O:25]>N1C=CC=CC=1>[F:22][C:3]1[CH:4]=[C:5]([F:21])[C:6]([C:8]2[C:9]([CH3:20])=[N:10][C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH3:19])[CH:12]=3)=[CH:7][C:2]=1[NH:1][C:24](=[O:25])[O:26][C:27]([CH3:29])=[CH2:28]

Participants

4

Reactant 2

HCID 93846Isopropenyl chloroformateHCID 89815338HCID 89815338, compound

Product 1

HCID 89815666HCID 89815666, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Treat a 0° C. solution of 3-(5-amino-2,4-difluorophenyl)-N,2-dimethyl-1,6-naphthyridin-7-amine (1.45 g, 4.83 mmol) in pyridine (30 mL) drop-wise with isopropenyl chloroformate (0.528 mL, 4.83 mmol), warm to RT and stir overnight. Add EtOAc, wash with satd. NaHCO3 (2×), dry, concentrate and purify by silica gel chromatography (EtOAc/TEA pre-wash, EtOAc/Hex) to afford the title compound (1.449 g, 78%). 1H NMR (400 MHz, DMSO-d6): δ 9.77 (s, 1H), 8.85 (s, 1H), 8.03 (s, 1H), 7.67-7.63 (m, 1H), 7.49 (t, 1H), 6.87-6.84 (m, 1H), 6.52 (s, 1H), 4.73 (s, 1H), 4.70 (s, 1H), 2.82 (d, 3H), 2.38 (s, 3H), 1.91 (s, 3H); MS (ESI) m/z: 385.2 (M+H+).

Workup

  1. washAdd EtOAc, wash with satd
  2. dry with materialNaHCO3 (2×), dry
  3. concentrationconcentrate
  4. custompurify by silica gel chromatography (EtOAc/TEA pre-wash, EtOAc/Hex)

Sources & evidence

ORD record
ord-632b926f87314c2d89fe631d7344051b
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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