Water → HCID 89827768, compound

HRID 715137Notes

Reaction equation

HRID 715137 reaction equation
C=C(O[C:5](=[O:27])[NH:6][C:7]1[CH:12]=[C:11]([C:13]2[C:14]([CH3:24])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][N:19]=[C:18]([Cl:23])[CH:17]=3)[C:10]([CH3:25])=[CH:9][C:8]=1[F:26])C.Cl.[F:29][C:30]([F:35])([F:34])[CH2:31][CH2:32][NH2:33].CN1CCCC1.O>C1COCC1>[Cl:23][C:18]1[CH:17]=[C:16]2[C:21]([CH:22]=[C:13]([C:11]3[C:10]([CH3:25])=[CH:9][C:8]([F:26])=[C:7]([NH:6][C:5]([NH:33][CH2:32][CH2:31][C:30]([F:35])([F:34])[F:29])=[O:27])[CH:12]=3)[C:14]([CH3:24])=[N:15]2)=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 84541-MethylpyrrolidineHCID 252105053,3,3-Trifluoropropylamine hydrochlorideHCID 89827812HCID 89827812, compound

Product 1

HCID 89827768HCID 89827768, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Heat a mixture of prop-1-en-2-yl(5-(7-chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluoro-4-methylphenyl)carbamate (0.20 g, 0.518 mmol), 3,3,3-trifluoropropylamine hydrochloride (0.093 g, 0.622 mmol) and 1-methylpyrrolidine (0.068 mL, 0.648 mmol) in THF (5 mL) at 55° C. overnight. Cool to RT, add H2O, extract with EtOAc (2×), wash the combined organics with brine (2×), dry over MgSO4 and concentrate to dryness to afford the title compound (220 mg, 96%). 1H NMR (400 MHz, DMSO-d6): δ 9.23 (s, 1H), 8.53 (s, 1H), 8.31 (s, 1H), 8.01 (s, 1H), 7.97 (d, J=8.4 Hz, 1H), 7.23 (d, J=12.3 Hz, 1H), 6.75 (t, J=5.9 Hz, 1H), 3.58-3.02 (m, 2H), 2.42 (m, 2H), 2.41 (s, 3H), 1.95 (s, 3H).

Workup

  1. temperatureHeat
  2. extractionextract with EtOAc (2×)
  3. washwash the combined organics with brine (2×)
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-1a93ee7db92f4042ac4b9f37c0aca395
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

Loading…