Sodium hydride → HCID 21101717, compound

HRID 1353431Notes

Reaction equation

HRID 1353431 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([OH:28])[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[F:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]4[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]([O:28][CH2:36][C:35]5[CH:38]=[CH:39][C:32]([F:31])=[CH:33][CH:34]=5)[CH2:22]4)=[O:19])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 21101724HCID 21101724, compound

Product 1

HCID 21101717HCID 21101717, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

As described for example 138, 4-(7-chloro-4-quinolinyl)-N-(3-hydroxycycloheptyl)-1-piperazinecarboxamide (50 mg, 0.124 mmol), NaH (8.9 mg, 0.37 mmol), and 4-fluorobenzyl bromide (28.2 mg, 0.15 mmol) are reacted to give the title product after flash chromatography with CH2Cl2-MeOH. LC-MS: 511 (M++1). 1H NMR (CDCl3) δ 8.75 (d, 1H), 8.05 (s, 1H), 7.95 (d, 1H), 7.45 (d, 1H), 7.35 (m, 2H), 7.00 (m, 2H), 6.85 (d, 1H), 4.50 (m, 2H), 4.40 (m, 1H), 4.10 (m, 1H), 3.65 (m, 4H), 3.20 (m, 4H), 2.20 (m, 1H), 2.10 (m, 1H), 1.50–1.90 (m, 6H), 1.40 (m, 2H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-c4783f164dda4636b95965b28734bf50
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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