Phenyl N-hydroxycarbamate → 4-[(1H-Benzoimidazol-4-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-piperidine-1-carboxylic acid hydroxyamide

HRID 1592568Notes

Reaction equation

HRID 1592568 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][N:11]([CH2:18][C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:4]=2[N:3]=[CH:2]1.[O:26]([C:33]([NH:35][OH:36])=O)C1C=CC=CC=1>C1COCC1>[OH:36][NH:35][C:33]([N:15]1[CH2:14][CH2:13][CH:12]([N:11]([CH2:10][C:9]2[C:4]3[N:3]=[CH:2][NH:1][C:5]=3[CH:6]=[CH:7][CH:8]=2)[CH2:18][C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:17][CH2:16]1)=[O:26]

Participants

4

Reactant 2

HCID 148233Phenyl N-hydroxycarbamateHCID 67273179(1H-Benzoimidazol-4-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine

Product 1

HCID 589970024-[(1H-Benzoimidazol-4-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-piperidine-1-carboxylic acid hydroxyamideYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a THF solution (3 mL) of the amine from above (100 mg, 0.300 mmol) was added N-(Phenoxycarbonyl)hydroxylamine (54.8 mg, 0.360 mmol), and the resultant solution was heated to 80° C. for 7 h and stirred at room temperature for 66 h. The solution was concentrated to dryness and the crude material was purified by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 80:10:10) to afford COMPOUND 288 (49 mg, 55%) as a white solid.

Workup

  1. concentrationThe solution was concentrated to dryness
  2. customthe crude material was purified by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 80:10:10)

Sources & evidence

ORD record
ord-6d4e15f900254b4f8cf6ec787f8967d2
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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