Pyridine → HCID 178432494, compound

HRID 13243Notes

Reaction equation

HRID 13243 reaction equation
[C:1]([O:4]C(=O)C)(=O)[CH3:2].[C:8]([C:10]1[CH:38]=[CH:37][CH:36]=[CH:35][C:11]=1[O:12][C:13]1[C:27]([O:28][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[CH:26][C:16]2[NH:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:19][C:15]=2[CH:14]=1)#[N:9].[N:39]1C=CC=CC=1>>[N:31]1[CH:32]=[CH:33][CH:34]=[C:29]([O:28][C:27]2[C:13]([O:12][C:11]3[CH:35]=[CH:36][CH:37]=[CH:38][C:10]=3[C:8]3[N:39]=[C:1]([CH3:2])[O:4][N:9]=3)=[CH:14][C:15]3[NH:19][C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)=[N:17][C:16]=3[CH:26]=2)[CH:30]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 231456625-(2-Cyano-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole

Product 1

HCID 178432494HCID 178432494, compound

Conditions

Temperature
60 °C

Procedure

0.3 ml of acetic anhydride was added to a pyridine (0.5 ml) solution of 20 mg of 5-(2-(N-hydroxycarbaminidoyl)-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole obtained in the same manner as in Example 61 but using 5-(2-cyano-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole obtained in Example 5, and the reaction liquid was stirred overnight at 60° C. The solvent was evaporated away under reduced pressure, and this was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a pale yellow solid.

Workup

  1. customobtained in the same manner as in Example 61
  2. customthe reaction liquid
  3. customThe solvent was evaporated away under reduced pressure
  4. customthis was purified
  5. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-a648d8640335409eb0ed64fedd81330e
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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