Isopropanol → HCID 18671514, compound

HRID 276783Notes

Reaction equation

HRID 276783 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:15]=[C:16]([C:20]2[NH:24][C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([N:31]4[CH2:36][CH2:35][N:34]([CH:37]([CH3:39])[CH3:38])[CH2:33][CH2:32]4)[CH:26]=3)=[N:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1.[C:40]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:45]=CC=C[CH:41]=1.C(O)(C)C>ClCCl>[CH:40]([O:13][C:14]1[CH:15]=[C:16]([C:20]2[NH:24][C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([N:31]4[CH2:32][CH2:33][N:34]([CH:37]([CH3:39])[CH3:38])[CH2:35][CH2:36]4)[CH:26]=3)=[N:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1)([CH3:45])[CH3:41]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18671523HCID 18671523, compound

Product 1

HCID 18671514HCID 18671514, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl azodicarboxylate (0.22 mL) was added via syringe to a solution of 1-{4-[5-(3-Hydroxy-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isopropyl-piperazine (304 mg) and triphenylphosphine (0.371 g) in a 1:1 mixture of isopropanol and dichloromethane (13 mL). The resultant solution was stirred at ambient temperature for 3 days and then washed with water. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (5% methanol in dichloromethane) to provide 1-{4-[5-(3-Isopropoxy-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isopropyl-piperazine (0.112 g).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-029082a98ecc4fd1b0b8a9fef891babe
Source dataset
uspto-grants-2002_03
Patent number
US06355635B1

Reaction notes

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