Sodium hydride → HCID 17757773, compound

HRID 898143Notes

Reaction equation

HRID 898143 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20](=[O:28])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[F:31][C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4([C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[NH:21][C:20](=[O:28])[O:19]4)[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[C:35](=[O:36])[C:34]2[CH:38]=[CH:39][CH:40]=[C:32]([F:31])[CH:33]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 743763-Fluorobenzoyl chlorideHCID 17757748HCID 17757748, compound

Product 1

HCID 17757773HCID 17757773, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg (0.252 mmol) 1′-[(6-chloro-1H-indol-3-yl)carbonyl]spiro[3,1-benzoxazine-4,4′-piperidin]-2(1H)-one (described in example 1) in dry DMF (5 ml) was added 10 mg NaH (0.25 mmol, 60% in oil). After 15 minutes at RT, 43.9 mg (0.277 mmol) of 3-fluoro-benzoyl chloride was added and stirring continued overnight. The reaction mixture was poured onto an aqueous solution of ammonium chloride, and the product extracted twice with ethyl acetate. The combined organic phases were dried on Na2SO4 and the solvent evaporated under reduced pressure. Purification by preparative HPLC yielded 1′-{[6-chloro-1-(3-fluorobenzoyl)-1H-indol-3-yl]carbonyl}spiro[3,1-benzoxazine-4,4′-piperidin]-2(1H)-one.

Workup

  1. extractionthe product extracted twice with ethyl acetate
  2. customThe combined organic phases were dried on Na2SO4
  3. customthe solvent evaporated under reduced pressure
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-1acb0a7712ee4f36a2c620e4a1df54e9
Source dataset
uspto-grants-2008_04
Patent number
US07351706B2

Reaction notes

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