Imidazole → HCID 22110953, compound

HRID 565397Notes

Reaction equation

HRID 565397 reaction equation
P(Cl)(Cl)(Cl)=O.CC(OC([N:13]1[CH:22]([C:23]([N:25]2[CH2:29][CH2:28][CH2:27][CH:26]2[C:30]([NH2:32])=O)=[O:24])[CH2:21][C:20]2[C:15](=[CH:16][C:17]([O:35][CH3:36])=[C:18]([O:33][CH3:34])[CH:19]=2)[CH2:14]1)=O)(C)C.N1C=CN=C1>N1C=CC=CC=1>[CH3:34][O:33][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[O:35][CH3:36])[CH2:14][NH:13][CH:22]([C:23]([N:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[C:30]#[N:32])=[O:24])[CH2:21]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24813Phosphorus oxychlorideHCID 70245189HCID 70245189, compound

Product 1

HCID 22110953HCID 22110953, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phosphorus oxychloride (239 mg, 0.15 mL, 1.56 mmol) was added to a solution of the title D compound of Example 6, 3-(2-aminocarbonyl-1-pyrrolidinyl)carbonyl-3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinecarboxylic acid 2-(1,1-dimethylethyl) ester (259 mg, 0.6 mmol; diastereomer B) and imidazole (53 mg, 0.78 mmol) in pyridine (6 mL) at −45° C. The reaction was stirred for 1.75 hours, then allowed to stand at 8° C. overnight, after which the mixture was concentrated under vacuum. The residue was purified by flash chromatography on silica gel using 2% methanol in methylene chloride as eluent to give 205 mg of the title compound as a yellowish white solid.

Workup

  1. waitto stand at 8° C. overnight
  2. concentrationafter which the mixture was concentrated under vacuum
  3. customThe residue was purified by flash chromatography on silica gel using 2% methanol in methylene chloride as eluent

Sources & evidence

ORD record
ord-acd566a2f6834ca79c57a9d8f4ca3d08
Source dataset
uspto-grants-2001_01
Patent number
US06172081B2

Reaction notes

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