2-Phenyl-4-carboxythiazole → N-(2-(6-(morpholinomethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-2-phenylthiazole-4-carboxamide

HRID 1799127Notes

Reaction equation

HRID 1799127 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]3[N:16]=[C:15]([C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[NH2:19])[S:14][C:11]3=[N:12][CH:13]=2)[CH2:3][CH2:2]1.[C:24]1([C:30]2[S:31][CH:32]=[C:33]([C:35](O)=[O:36])[N:34]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]3[N:16]=[C:15]([C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[NH:19][C:35]([C:33]4[N:34]=[C:30]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[S:31][CH:32]=4)=[O:36])[S:14][C:11]3=[N:12][CH:13]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 1389282-Phenyl-4-carboxythiazoleHCID 585518812-(6-(Morpholinomethyl)thiazolo[5,4-b]pyridin-2-yl)aniline

Product 1

HCID 46245045N-(2-(6-(morpholinomethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-2-phenylthiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared according to amide synthesis general method A, utilizing 2-(6-(morpholinomethyl)thiazolo[5,4-b]pyridin-2-yl)aniline and 2-phenylthiazole-4-carboxylic acid. The product was isolated by precipitation by the addition of water, triturated with hot methanol, dissolved in CH2Cl2, washed with dilute NaHCO3, concentrated and purified by silica gel chromatography (gradient 0 to 10% methanol in CH2Cl2). MS Calcd for C27H23N5O2S2: 513.13. Found (M+H)+ m/z=514.

Workup

  1. customtriturated with hot methanol
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with dilute NaHCO3
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (gradient 0 to 10% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-844a7d3769c54253ad4c379b124701bc
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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