Tetrahydrofuran → N-[(1R)-1-[[(4S)-4-(4-Chlorophenyl)-4-hydroxy-3,3-dimethyl-1-piperidinyl]carbonyl]-2-methylpropyl]-N′-methylurea

HRID 1016132Notes

Reaction equation

HRID 1016132 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].Cl.[NH2:6][C@H:7]([CH:26]([CH3:28])[CH3:27])[C:8]([N:10]1[CH2:15][CH2:14][C@@:13]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)([OH:16])[C:12]([CH3:25])([CH3:24])[CH2:11]1)=[O:9].C1COCC1>C(N(CC)CC)C>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C@@:13]2([OH:16])[CH2:14][CH2:15][N:10]([C:8](=[O:9])[C@H:7]([NH:6][C:3]([NH:2][CH3:1])=[O:4])[CH:26]([CH3:28])[CH3:27])[CH2:11][C:12]2([CH3:24])[CH3:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12228Methyl IsocyanateHCID 67299922HCID 67299922, compound

Product 1

HCID 57888697N-[(1R)-1-[[(4S)-4-(4-Chlorophenyl)-4-hydroxy-3,3-dimethyl-1-piperidinyl]carbonyl]-2-methylpropyl]-N′-methylurea

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A reaction tube was charged with methyl isocyanate (3 μL), (R)-2-amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride (20 mg) and THF (2 mL). Triethylamine (7.4 μL) was added and the reaction mixture was shaken overnight at rt. After this time, the resulting solution concentrated and purified by preparative silica gel chromatography (100% EtOAc to 20% MeOH/CH2Cl2) to provide Example 510. MS found: (M+H)+=396.3.

Workup

  1. concentrationAfter this time, the resulting solution concentrated
  2. custompurified by preparative silica gel chromatography (100% EtOAc to 20% MeOH/CH2Cl2)
  3. customto provide Example 510

Sources & evidence

ORD record
ord-b7e643d71a484422ba0b5e98c99f2e0a
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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