GR 127935 → HCID 10600871, compound

HRID 1742621Notes

Reaction equation

HRID 1742621 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:28]=[C:27]([CH3:29])[O:26][N:25]=4)=[CH:20][C:19]=3[CH3:30])=[CH:14][CH:13]=2)=[O:11])=[CH:5][C:4]=1[N:31]1[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]1.Cl.N1C=CC=CC=1>C(=O)(O)[O-].[Na+]>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:28]=[C:27]([CH3:29])[O:26][N:25]=4)=[CH:20][C:19]=3[CH3:30])=[CH:16][CH:17]=2)=[O:11])=[CH:5][C:4]=1[N:31]1[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 107780GR 127935HCID 10176127Pyridinium chloride

Product 1

HCID 10600871HCID 10600871, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of the product of Example 1 (91 mg) and pyridine hydrochloride (2 g) was heated to 180°-190° for 8 h. Sodium bicarbonate (8%; 30 ml) was added and the mixture extracted with dichloromethane (2×25 ml). The dried extracts were evaporated to give a dark oil. This material was chromatographed on silica gel (Merck 7729, 10 g) eluting with System A (200:8:1) to give the title compound as a colourless foam (27 mg).

Workup

  1. temperaturewas heated to 180°-190° for 8 h
  2. extractionthe mixture extracted with dichloromethane (2×25 ml)
  3. customThe dried extracts were evaporated
  4. customto give a dark oil
  5. customThis material was chromatographed on silica gel (Merck 7729, 10 g)
  6. washeluting with System A (200:8:1)

Sources & evidence

ORD record
ord-d0aaebfb9959443bb067c21be2f18fa3
Source dataset
uspto-grants-1994_08
Patent number
US05340810

Reaction notes

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