Isopropanol → HCID 18671514, compound

HRID 1057317Notes

Reaction equation

HRID 1057317 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). MS m/z 420 (M++1).

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-211affe540f04340b3f202732f1c136c
Source dataset
uspto-grants-2003_02
Patent number
US06514966B2

Reaction notes

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