Tetrahydrofuran → HCID 67957698, compound

HRID 1189649Notes

Reaction equation

HRID 1189649 reaction equation
[OH:1][C:2]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)([CH3:4])[CH3:3].[H-].[Na+].C1COCC1.[F:18][C:19]([F:37])([F:36])[CH2:20][NH:21][C:22](=[O:35])[C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[C:26]([NH:32][CH3:33])=[CH:25][C:24]=1F>CCOC(C)=O>[F:18][C:19]([F:36])([F:37])[CH2:20][NH:21][C:22](=[O:35])[C:23]1[CH:28]=[C:27]([N+:29]([O-:31])=[O:30])[C:26]([NH:32][CH3:33])=[CH:25][C:24]=1[N:8]1[CH2:9][CH2:10][CH:5]([C:2]([OH:1])([CH3:4])[CH3:3])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 52003212-(4-Piperidyl)-2-propanolHCID 67957626HCID 67957626, compound

Product 1

HCID 67957698HCID 67957698, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(1-hydroxy-1-methyl-ethyl)-piperidine (24 mg, 0.17 mmol), NaH-suspension (50% in mineral oil, 8 mg, ˜0.17 mmol) and THF (1 mL) is stirred for 10 min. Then, N-(2,2,2-trifluoro-ethyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide is added and it is stirred for 1.5 h. The mixture is diluted with EtOAc, washed with water, concentrated, dried and directly used in the next step.

Workup

  1. stirringit is stirred for 1.5 h
  2. washwashed with water
  3. concentrationconcentrated
  4. customdried

Sources & evidence

ORD record
ord-7fb71ffb9c31486b9a7d29cf53560e8a
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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