Water → HCID 24957868, compound

HRID 502248Notes

Reaction equation

HRID 502248 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:32])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([CH:28]3[CH2:31][CH2:30][CH2:29]3)[C:16]3[C:21]([C:22]=2[C:23]#[N:24])=[CH:20][CH:19]=[C:18]([O:25][CH2:26][CH3:27])[CH:17]=3)=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH:28]1([N:15]2[C:16]3[C:21](=[CH:20][CH:19]=[C:18]([O:25][CH2:26][CH3:27])[CH:17]=3)[C:22]([C:23]#[N:24])=[C:14]2[C:11]2[CH:12]=[CH:13][C:8]([N:7]3[CH2:2][CH2:3][CH2:4][O:5][C:6]3=[O:32])=[CH:9][CH:10]=2)[CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 49771961HCID 49771961, compound

Product 1

HCID 24957868HCID 24957868, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indole-2-yl)-phenyl]-carbamic acid 3-chloro-propyl ester in 5 mL of DMF is added anhydrous K2CO3. The resulting mixture is stirred at 80° C. until complete consumption of the starting material is determined by TLC. After cooling, 10 mL of water is added to the reaction mixture to afford a solid precipitation which is collected by filtration, followed by washing with ether. The desired 1-cyclobutyl-6-ethoxy-2-[4-(2-oxo-[1,3]oxazinan-3-yl)-phenyl]-1H-indole-3-carbonitrile is obtained as a white powder (76.2 mg, 91.8% yield).

Workup

  1. temperatureAfter cooling
  2. customto afford
  3. customa solid precipitation which
  4. filtrationis collected by filtration
  5. washby washing with ether

Sources & evidence

ORD record
ord-e696a311a7ce49e49d46004a933fc2e5
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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