Sodium hydride → HCID 66874570, compound

HRID 249890Notes

Reaction equation

HRID 249890 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[H-].[Na+].Cl[C:18]1[O:19][C:20]2[C:21](=[C:23]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:25][CH:26]=2)[N:22]=1>C1COCC1>[C:11]([O:10][C:8]([N:3]1[CH2:4][CH2:5][N:6]([C:18]2[O:19][C:20]3[C:21](=[C:23]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:25][CH:26]=3)[N:22]=2)[CH2:7][CH:2]1[CH3:1])=[O:9])([CH3:13])([CH3:12])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15087784tert-Butyl 2-methylpiperazine-1-carboxylateHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66874570HCID 66874570, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 2-methylpiperazine-1-carboxylate (340 mg, 1.70 mmol) in THF (5 mL) was added sodium hydride (60%, 82 mg, 2.04 mmol). The reaction mixture was stirred at room temperature for 5 min, then methyl 2-chlorobenzoxazole-4-carboxylate (300 mg, 1.41 mmol) in THF (5 mL) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 19 h. The mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography (silica gel, 20% EtOAc in hexane) to afford methyl 2-(4-(tert-butoxycarbonyl)-3-methylpiperazin-1-yl)benzoxazole-4-carboxylate (336 mg, 63%) as yellow solid. MS consistent.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 19 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by column chromatography (silica gel, 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-c002f4d83506458fbda81fce746792cc
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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