Sodium hydride → HCID 66674083, compound

HRID 421810

Reaction equation

HRID 421810 reaction equation
[CH:1]1([C:7]([C:9]2[CH:10]([C:27]3[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=3)[NH:11][C:12](=[O:26])[N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[C:14]=2[CH3:15])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42]>C1COCC1>[CH:1]1([C:7]([C:9]2[CH:10]([C:27]3[CH:28]=[CH:29][C:30]([C:31]#[N:32])=[CH:33][CH:34]=3)[N:11]([CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])[C:12](=[O:26])[N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:23])[F:24])[CH:17]=3)[C:14]=2[CH3:15])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 706082-Bromo-N,N-diethylethanamineHCID 59684783HCID 59684783, compound

Product 1

HCID 66674083HCID 66674083, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 21 (780 mg, 1.67 mmol) in THF (25 ml) is added sodium hydride (60% dispersion in mineral oil; 653 mg, 2.53 mmol). The mixture is stirred for 1 hour at room temperature, then 2-bromo-N,N-diethylethanamine (653 mg, 2.53 mmol) is added, and the solution is stirred overnight (16 h) at room temperature. The reaction mixture is quenched with methanol (10 ml), concentrated, and the crude product is purified by preparative HPLC.

Workup

  1. stirringthe solution is stirred overnight (16 h) at room temperature
  2. customThe reaction mixture is quenched with methanol (10 ml)
  3. concentrationconcentrated
  4. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-687052fa5a1d4a5e90cd74506f7ac943
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Linked notes

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