Diisopropylethylamine → 5-(3-methoxypropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

HRID 453318Notes

Reaction equation

HRID 453318 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17](Cl)=[O:18].[N:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[S:22][C:21]=1[C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH2:31].CCN(C(C)C)C(C)C>C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([NH:31][C:30]1[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=1[C:21]1[S:22][C:23]2[C:28]([N:20]=1)=[CH:27][CH:26]=[CH:25][N:24]=2)=[O:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581014682-(Thiazolo[5,4-b]pyridin-2-yl)anilineHCID 585518965-(3-Methoxypropyl)-2-phenylthiazole-4-carbonyl chloride

Product 1

HCID 462450495-(3-methoxypropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamideYield 86.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(3-methoxypropyl)-2-phenylthiazole-4-carbonyl chloride (229 mg, 0.774 mmol) was added to a suspension of 2-(thiazolo[5,4-b]pyridin-2-yl)aniline (141 mg, 0.619 mmol) in acetonitrile (15 mL). DIPEA (162 μL, 0.929 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The resulting ppt was collected by filtration, and rinsed with acetonitrile to give the title compound as a white solid (260 mg, 86% yield). MS Calcd for C26H22N4O2S2: 486.12. Found (M+H)+ m/z=487.

Workup

  1. filtrationThe resulting ppt was collected by filtration
  2. washrinsed with acetonitrile

Sources & evidence

ORD record
ord-c4cdda3c83784aa5bf598a4b035105e2
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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