Sodium hydride → HCID 11692684, compound

HRID 2080341Notes

Reaction equation

HRID 2080341 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+].[CH3:55][O:56][CH2:57][CH2:58]Br>CN(C=O)C>[F:52][C:28]1[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][N:38]3[CH2:43][CH2:42][NH:41][C@@H:40]([CH3:51])[CH2:39]3)[CH:32]=2)=[CH:30][C:25]([CH2:24][N:23]([CH2:58][CH2:57][O:56][CH3:55])[C:21](=[O:22])[C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:16]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 67100907HCID 67100907, compound

Product 1

HCID 11692684HCID 11692684, compoundYield 27.3%

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 (76.1 mg, 0.106 mmol), NaH (8.29 mg, 0.345 mmol) and 2-bromoethyl methyl ether (0.015 mL, 0.160 mmol) in DMF (1.0 mL) were reacted to give the desired product (16.6 mg, 27.2%). EI-MS m/z 573(M−H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ee0878b88cd64b5a9f9a75a6e6004c44
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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