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

HRID 453302Notes

Reaction equation

HRID 453302 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:16](Cl)=[O:17].CCN(C(C)C)C(C)C.[N:28]1[C:36]2[C:31](=[N:32][CH:33]=[CH:34][CH:35]=2)[S:30][C:29]=1[C:37]1[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=1[NH2:39]>CC#N>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:16]([NH:39][C:38]1[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=1[C:29]1[S:30][C:31]2[C:36]([N:28]=1)=[CH:35][CH:34]=[CH:33][N:32]=2)=[O:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581014682-(Thiazolo[5,4-b]pyridin-2-yl)anilineHCID 585519005-(3-Chloropropyl)-2-phenylthiazole-4-carbonyl chloride

Product 1

HCID 585518955-(3-chloropropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamideYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 5-(3-chloropropyl)-2-phenylthiazole-4-carbonyl chloride (906 mg, 3.2 mmol), DIPEA (1.1 mL, 6.4 mmol), and 2-(thiazolo[5,4-b]pyridin-2-yl)aniline b (585 mg, 2.6 mmol) in CH3CN (12 mL) was stirred for 16 h. The resulting ppt was collected by filtration, rinsed with CH3CN and dried. The crude product was purified by MPLC eluting with DCM/MeOH (0-5% gradient) to give 5-(3-chloropropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (316 mg, 26% yield).

Workup

  1. filtrationThe resulting ppt was collected by filtration
  2. washrinsed with CH3CN
  3. customdried
  4. customThe crude product was purified by MPLC
  5. washeluting with DCM/MeOH (0-5% gradient)

Sources & evidence

ORD record
ord-f429aab7ba374300b2e68ca28f91823a
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

Loading…