Sodium hydride → HCID 68868458, compound

HRID 729991Notes

Reaction equation

HRID 729991 reaction equation
[CH2:1]([NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([C:15]2[C:16]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[N:17][NH:18][CH:19]=2)[N:7]=1)[CH:2]([CH3:4])[CH3:3].[H-].[Na+].Cl.[O:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37]Cl)[CH2:32][CH2:31]1>CN(C=O)C>[CH2:1]([NH:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([C:15]2[C:16]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)=[N:17][NH:18][C:19]=2[CH:36]([N:33]2[CH2:34][CH2:35][O:30][CH2:31][CH2:32]2)[CH3:37])[N:7]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178448861HCID 178448861, compound

Product 1

HCID 68868458HCID 68868458, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat a solution of 2-isobutylamino-3-nitro-6-[3-(4-fluorophenyl)pyrazol-4-yl]pyridine (1.25 g, 3.52 mmol) in dry DMF (15 mL) with 95% NaH (0.36 g, 14.3 mmol) at 0° C. for 15 min. Add morpholinoethylchloride hydrochloride (0.983 g, 5.28 mmol) and slowly warm to RT. Add additional NaH (0.36 g, 14.3 mmol), after 1 h and stir the reaction mixture for 24 h. Quench with MeOH (1 mL) and dilute with water (30 mL). Extract with EtOAc (100 mL), dry with MgSO4, and concentrate. Purify the residue (silica gel chromatography, eluting with hexanes:EtOAc 1:2) to give the title compound (1.35 g, 81%).

Workup

  1. customQuench with MeOH (1 mL)
  2. additiondilute with water (30 mL)
  3. extractionExtract with EtOAc (100 mL)
  4. dry with materialdry with MgSO4
  5. concentrationconcentrate
  6. customPurify
  7. washthe residue (silica gel chromatography, eluting with hexanes:EtOAc 1:2)

Sources & evidence

ORD record
ord-e24db80e273e491f9753ab531cd02256
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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