Hexane → N-[(2-isopropoxyphenyl)methyl]thiazolo[5,4-c]pyridine-2-carboxamide

HRID 1383420Notes

Reaction equation

HRID 1383420 reaction equation
C(O[C:4]([C:6]1[S:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[N:14]=1)=[O:5])C.[CH:15]([O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22])([CH3:17])[CH3:16].C[Al](C)C.CCCCCC>ClCCl>[CH:15]([O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH:22][C:4]([C:6]1[S:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[N:14]=1)=[O:5])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 8058HexaneHCID 7358931-(2-Isopropoxyphenyl)methanamineHCID 14252940Ethyl thiazolo[5,4-c]pyridine-2-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 9927392N-[(2-isopropoxyphenyl)methyl]thiazolo[5,4-c]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of thiazolo [5,4-c]pyridine-2-carboxylic acid ethyl ester (34 mg, 0.16 mmol) and 2-isopropoxy benzyl amine (67 mg, 0.41 mmol)in dichloromethane(1.7 mL) was added a solution of trimethylaluminum in hexane(0.203 mL, 2.0 M., 0.41 mmol). The solution was then stirred for 5 hours at room temperature. After usual work-up, the product was purified by flash chromatography (CH2Cl2/EtOAc 2:1) to give 30 mg of the thiazolo derivative.

Workup

  1. customAfter usual work-up, the product was purified by flash chromatography (CH2Cl2/EtOAc 2:1)
  2. customto give 30 mg of the thiazolo derivative

Sources & evidence

ORD record
ord-b90ff3c0c5d14f588e0e7ccdfda44fed
Source dataset
uspto-grants-2001_07
Patent number
US06255318B1

Reaction notes

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