Dimethylformamide → HCID 57936304, compound

HRID 1435032Notes

Reaction equation

HRID 1435032 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]4[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]4)[N:13]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].CN(C=O)C.Br[CH2:37][C:38]#[N:39]>C1COCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]4[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]4)[N:13]=3)=[CH:8][N:9]2[CH2:37][C:38]#[N:39])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 57936207HCID 57936207, compound

Product 1

HCID 57936304HCID 57936304, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [4-(6-Methoxy-1H-indol-3-yl)-pyrimidin-2-yl]-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (150 mg, 0.40 mmol) in 2 ml of THF was added to a suspension of sodium hydride (55.3 mg, 1.38 mmol, 60% mineral dispersion) in 2 ml of THF. 0.1 ml of DMF was added and stirring was continued for 15 minutes. Bromoacetonitrile (51.9 mg, 0.43 mmol) was then added and the solution was stirred for 5 hours. The solvent was removed and the residue was purified by flash chromatography on silicagel (EtOAc/MeOH/ammonia:5/1/0.05) to give the title compound. Yield: 142 mg (88%).

Workup

  1. stirringthe solution was stirred for 5 hours
  2. customThe solvent was removed
  3. customthe residue was purified by flash chromatography on silicagel (EtOAc/MeOH/ammonia:5/1/0.05)

Sources & evidence

ORD record
ord-b9ead81564484c9b937c11a8b2261e4e
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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