Sodium hydride → HCID 53630426, compound

HRID 1864174Notes

Reaction equation

HRID 1864174 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][CH2:16][CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:21]1[C:22]2[O:29][N:28]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=3)[C:23]=2[N:24]=[CH:25][N:26]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][N:15]([CH2:16][CH3:17])[C:21]2[C:22]3[O:29][N:28]=[C:27]([C:30]4[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=4)[C:23]=3[N:24]=[CH:25][N:26]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 218975727-Chloro-3-[4-(methanesulfonyl)phenyl][1,2]oxazolo[4,5-d]pyrimidineHCID 53249196tert-Butyl 4-[(ethylamino)methyl]piperidine-1-carboxylate

Product 1

HCID 53630426HCID 53630426, compoundYield 324.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Ethylaminomethyl-piperidine-1-carboxylic acid tert-butyl ester (0.12 g, 0.49 mmol) was dissolved in anhydrous THF (5 mL) and treated with NaH, 60% oil dispersion (20 mg, 0.49 mmol) at ambient temperature. After stirring for 10 min, 7-chloro-3-(4-methanesulfonyl-phenyl)-isoxazolo[4,5-d]pyrimidine (0.15 g, 0.49 mmol) was added. The reaction was stirred for 3 h and concentrated under vacuum. The residue was subjected to SiO2 with ethyl acetate and hexane (1/1) to afford Compound D2 (0.82 g, 61%). 1H NMR (400Mz, DMSO-d6) δ 8.49 (s, 1H), 8.41 (d, J=7.1, 2H), 8.34 (d, J=7.1, 2H), 4.10˜3.74 (m, 7H), 3.52 (m, 1H), 3.25 (t, 3H), 1.41˜1.22 (m, 4H). LCMS 516.3[M+H].

Workup

  1. stirringThe reaction was stirred for 3 h
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-69da6f6f6e3b42ba92bc532933c28f0c
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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