Sodium hydride → HCID 11685871, compound

HRID 2080339Notes

Reaction equation

HRID 2080339 reaction equation
CC(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:16]=[C:17]([C:21]([NH:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:52])=[C:29]([C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][N:38]5[CH2:43][CH2:42][N:41](C(OC(C)(C)C)=O)[C@@H:40]([CH3:51])[CH2:39]5)[CH:32]=4)[CH:30]=3)=[O:22])[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=O)(C)C.[H-].[Na+].Br[CH2:56][CH:57]1[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1>CN(C=O)C>[CH:57]1([CH2:56][N:23]([CH2:24][C:25]2[CH:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][N:38]4[CH2:43][CH2:42][NH:41][C@@H:40]([CH3:51])[CH2:39]4)[CH:32]=3)[C:28]([F:52])=[CH:27][CH:26]=2)[C:21](=[O:22])[C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:16]=2)[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137636Cyclohexane, (bromomethyl)-HCID 67100907HCID 67100907, compound

Product 1

HCID 11685871HCID 11685871, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the general procedure outlined in Example 66, 1,1-dimethylethyl (2S)-4-[(5′-{[({3-[(1-{[(1,1-dimethylethyl)oxy]carbonyl}-4-piperidinyl)methyl]phenyl}carbonyl)amino]methyl}-2′-fluoro-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate (47.3 mg, 0.0662 mmol), NaH (6.62 mg, 0.262 mmol) and (bromomethyl)cyclohexane (0.0150 mL, 0.108 mmol) in DMF (1.0 mL) were reacted to give the desired product (7.9 mg, 19.6%). EI-MS m/z 611 (M−H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c524b422b0d34243934a191028b8609b
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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