2-Phenyl-4-carboxythiazole → 2-phenyl-N-(2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

HRID 453314Notes

Reaction equation

HRID 453314 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[NH2:18])[S:13][C:10]3=[N:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]1([C:29]2[S:30][CH:31]=[C:32]([C:34](O)=[O:35])[N:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[C:23]1([C:29]2[S:30][CH:31]=[C:32]([C:34]([NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:14]3[S:13][C:10]4[C:9]([N:15]=3)=[CH:8][C:7]([CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:12][N:11]=4)=[O:35])[N:33]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 1389282-Phenyl-4-carboxythiazoleHCID 585518882-(6-(Pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)aniline

Product 1

HCID 462450462-phenyl-N-(2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared according to amide synthesis general method A, utilizing 2-(6-(pyrrolidin-1-ylmethyl)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 C27H23N5OS2: 497.13. Found (M+H)+ m/z=498.

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-a7ba312cc81249fa9a53dfa895106c31
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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