Sodium hydride → HCID 11578294, compound

HRID 2080337Notes

Reaction equation

HRID 2080337 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+].[C:55]1([O:61][CH2:62][CH2:63][CH2:64]Br)[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>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]([CH2:64][CH2:63][CH2:62][O:61][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=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)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68522Benzene, (3-bromopropoxy)-HCID 67100907HCID 67100907, compound

Product 1

HCID 11578294HCID 11578294, compoundYield 24.1%

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 (75.4 mg, 0.105 mmol), NaH (5.37 mg, 0.243 mmol) and 3-bromopropyl phenyl ether (0.020 mL, 0.127 mmol) in DMF (0.5 mL) were reacted to give the desired product (16.4 mg, 24.0%). EI-MS m/z 649(M−H)+.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c9c77d97dba94baaba3c6b294e550dae
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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