Sodium hydride → HCID 66967252, compound

HRID 1711853Notes

Reaction equation

HRID 1711853 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH2:17][C:18]1[C:19]([NH2:25])=[N:20][CH:21]=[C:22]([Br:24])[CH:23]=1)[CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)C.[H-].[Na+]>CS(C)=O.O>[Br:24][C:22]1[CH:21]=[N:20][C:19]2[NH:25][C:4](=[O:3])[CH2:5][N:6]([CH2:7][CH2:8][CH2:9][N:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[CH2:17][C:18]=2[CH:23]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 66967018HCID 66967018, compound

Product 1

HCID 66967252HCID 66967252, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of {(2-amino-5-bromo-pyridin-3-ylmethyl)-[3-(4-methyl-piperazin-1-yl)propyl]amino}acetic acid ethyl ester (0.50 g, 1.17 mmol) in DMSO (10 mL) was treated with NaH (60% dispersion in mineral oil, 47 mg, 1.17 mmol). After stirring at room temperature for 3 d, the mixture was diluted with H2O (30 mL) and then extracted with EtOAc (4×50 mL). The combined organic layers were dried over Na2SO4, filtered and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, CH2Cl2, MeOH, 92:8 to 87:13) gave the title compound (0.23 g, 51%) as a white solid: MS (ESI) m/e 382 (M+H)+.

Workup

  1. extractionextracted with EtOAc (4×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customPurification by flash column chromatography (silica gel, CH2Cl2, MeOH, 92:8 to 87:13)

Sources & evidence

ORD record
ord-04536ab0f24242a698cf6e824ca09449
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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