Hexane → Thiazolo[5,4-c]pyridine-2-carboxylic acid(1(s)-phenyl-ethyl)amide

HRID 1383422Notes

Reaction equation

HRID 1383422 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.[C:15]1([C@@H:21]([NH2:23])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[Al](C)C.CCCCCC>ClCCl>[C:15]1([C@@H:21]([NH:23][C:4]([C:6]2[S:7][C:8]3[CH:9]=[N:10][CH:11]=[CH:12][C:13]=3[N:14]=2)=[O:5])[CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 758181-Phenethylamine, (-)-HCID 14252940Ethyl thiazolo[5,4-c]pyridine-2-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 22980422Thiazolo[5,4-c]pyridine-2-carboxylic acid(1(s)-phenyl-ethyl)amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of thiazolo [5,4-c]pyridine-2-carboxylic acid ethyl ester (16 mg, 0.08 mmol) and 1(S)-phenyl ethyl amine (0.03 mL, 0.23 mmol)in dichloromethane(0.3 mL) was added a solution of trimethylaluminum in hexane(0.115 mL, 2.0 M., 0.23 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 1:1)and triturated in hexane to give 12 mg of the thiazolo derivative.

Workup

  1. customAfter usual work-up, the product was purified by flash chromatography (CH2Cl2/EtOAc 1:1)and
  2. customtriturated in hexane
  3. customto give 12 mg of the thiazolo derivative

Sources & evidence

ORD record
ord-e542642dd8d34120ace650b762ea1edb
Source dataset
uspto-grants-2001_07
Patent number
US06255318B1

Reaction notes

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