Dimethylformamide → HCID 11607005, compound

HRID 2080342Notes

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](C4C=CC=C(CN5CCN(C(OC(C)(C)C)=O)[C@@H](C)C5)C=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][CH2:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.[CH3:65][N:66]([CH:68]=O)[CH3:67]>>[F:52][C:28]1[C:29]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH2:65][N:66]3[CH2:68][CH2:13][NH:8][C@@H:9]([CH3:10])[CH2:67]3)[CH:20]=2)=[CH:30][C:25]([CH2:24][N:23]([CH2:56][CH2:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[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

Reactant 4

HCID 6228Dimethylformamide

HCID 12503(3-Bromopropyl)benzene

HCID 24758Sodium hydride

HCID 67100907HCID 67100907, compound

Product 1

HCID 11607005HCID 11607005, compoundYield 70%

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 (3-bromopropyl)benzene (0.024 mL, 0.160 mmol) in DMF (1.0 mL) were reacted to give the desired product (47.2 mg, 70.0%). EI-MS m/z 633(M−H)+.

Workup

customwere reacted

Sources & evidence

ORD record: ord-bf9b7d5da18f4851863f5b6d34f3a4e1
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932247B2

Reaction notes

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