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

HRID 1799116Notes

Reaction equation

HRID 1799116 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-32607501eda943ea894e0c9cb84dcfc2
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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