Water → SB-247853

HRID 427735Notes

Reaction equation

HRID 427735 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[NH:7][CH2:6][CH2:5]2.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30](=O)[O:31]C2C=CC=CC=2)=[CH:25][N:24]=1.C(N(CC)CC)C.O>C(#N)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([F:14])([F:12])[F:13])[N:7]([C:30](=[O:31])[NH:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=3)=[N:24][CH:25]=1)[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 105122695-Methyl-6-(trifluoromethyl)indolineHCID 11141770Phenyl N-[2-(pyridin-2-ylmethyloxy)pyridin-5-yl]carbamate

Product 1

HCID 9888804SB-247853Yield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of indoline (D13, 0.30 g, 1.49 mmol), phenylcarbamate (D3, 0.48 g, 1.5 mmol) and triethylamine (0.20 ml, 1.5 mmol) in dry acetonitrile (10 mL) was warmed briefly to ensure complete solution of reactants, then stirred overnight at room temperature. The mixture was poured into water (50 ml) and the precipitate was filtered off, washed with water and dried. The crude product was chromatographed on silica gel (25 g) eluted with 4% methanol/dichloromethane. Eluted product was recrystallised from dichloromethane/methanol to give the title compound (0.35 g, 55%), m.p. 219-20° C.

Workup

  1. temperaturewas warmed briefly
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried
  5. customThe crude product was chromatographed on silica gel (25 g)
  6. washeluted with 4% methanol/dichloromethane
  7. customEluted product was recrystallised from dichloromethane/methanol

Sources & evidence

ORD record
ord-b2fc7e526dd143bfb505662050c7d1bd
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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