4-Phenylthiazole-2-carboxylic acid → N-(2-(6-((4-(2-methoxyethyl)piperazin-1-yl)methyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-4-phenylthiazole-2-carboxamide

HRID 453309Notes

Reaction equation

HRID 453309 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:13]=[C:14]3[N:20]=[C:19]([C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[NH2:23])[S:18][C:15]3=[N:16][CH:17]=2)[CH2:7][CH2:6]1.[C:28]1([C:34]2[N:35]=[C:36]([C:39](O)=[O:40])[S:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:13]=[C:14]3[N:20]=[C:19]([C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[NH:23][C:39]([C:36]4[S:37][CH:38]=[C:34]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:35]=4)=[O:40])[S:18][C:15]3=[N:16][CH:17]=2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 38785394-Phenylthiazole-2-carboxylic acidHCID 585518702-(6-((4-(2-Methoxyethyl)piperazin-1-yl)methyl)thiazolo[5,4-b]pyridin-2-yl)aniline

Product 1

HCID 58551890N-(2-(6-((4-(2-methoxyethyl)piperazin-1-yl)methyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)-4-phenylthiazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared according to amide synthesis general method B, utilizing 2-(6-((4-(2-methoxyethyl)piperazin-1-yl)methyl)thiazolo[5,4-b]pyridin-2-yl)aniline and 4-phenylthiazole-2-carboxylic acid (1.5 eq). Addition of water to the crude reaction did not precipitate the product, therefore it was concentrated, triturated with hot MeCN, MeCN/EtOAc/MeOH mixture, and EtOAC/MeOH sequentially. The resulting pale yellow solid was lyophilized with a MeCN/water/HCl mixture and subsequently purified on prep HPLC. MS Calcd for C30H30N6O2S2: 570.19. Found (M+H)+ m/z=571.

Workup

  1. customreaction
  2. customdid not precipitate the product
  3. concentrationit was concentrated
  4. customtriturated with hot MeCN, MeCN/EtOAc/MeOH mixture, and EtOAC/MeOH sequentially
  5. customsubsequently purified on prep HPLC

Sources & evidence

ORD record
ord-d52ffd5fe2024aba9b4a303aa426f200
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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