Sodium hydride → HCID 87804050, compound

HRID 8228Notes

Reaction equation

HRID 8228 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[N:19][NH:20][C:21](=[O:33])[CH2:22][CH:23]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:24]Br)[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH2:26]([CH:23]1[CH2:24][N:20]([N:19]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)[C:21](=[O:33])[CH2:22]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 865926233-Benzyl-4-bromo-butyric acid(1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazide

Product 1

HCID 87804050HCID 87804050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-benzyl-4-bromo-butyric acid(1-pyridin-2-yl-2-quinolin-4-yl-ethylidene)-hydrazide (PREP. 70, 0.8 g, 1.6 mmol) in tetrahydrofuran (26 mL) at 0° C. is treated with NaH (60% in mineral oil, 0.086 g, 2.2 mmol). The mixture is warmed to room temperature and stirred for 2 h. Saturated ammonium chloride (2 mL) is added and volatiles removed in vacuo. The residue is chromatographed on SiO2 (90% ethyl acetate/hexanes followed by dichloromethane:methanol:ammonium hydroxide/94:5:1) to yield the title compound, 0.4 g (45%), as a yellowish foam.

Workup

  1. customvolatiles removed in vacuo
  2. customThe residue is chromatographed on SiO2 (90% ethyl acetate/hexanes followed by dichloromethane:methanol:ammonium hydroxide/94:5:1)

Sources & evidence

ORD record
ord-88fed48013e14196bee88628cda044de
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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