Dimethylformamide → HCID 86646061, compound

HRID 1800646Notes

Reaction equation

HRID 1800646 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[Cl:18][C:19]1[N:24]=[C:23]2[S:25][C:26]([NH2:28])=[N:27][C:22]2=[CH:21][CH:20]=1>ClCCl.O1CCCC1.O>[Cl:18][C:19]1[N:24]=[C:23]2[S:25][C:26]([NH:28][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:6])=[N:27][C:22]2=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 15655Cyclopropanecarboxylic acidHCID 65578Oxalyl chlorideHCID 42660645-chlorothiazolo[5,4-b]pyridin-2-amine

Product 1

HCID 86646061HCID 86646061, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyclopropanecarboxylic acid (129 mg, 1.50 mmol) in dichloromethane (5 mL) were added oxalyl chloride (190 mg, 1.50 mmol) and N,N-dimethylformamide (40 μL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was added to a solution (10 mL) of 5-chloro[1,3]thiazolo[5,4-b]pyridine-2-amine (185 mg, 1.00 mmol) in tetrahydrofuran at 0° C., and the mixture was stirred for 2 hr. To the reaction mixture was added water (10 mL), and the mixture was extracted with ethyl acetate (30 mL×3). The organic layer was concentrated under reduced pressure to give N-(5-chloro[1,3]thiazolo[5,4-b]pyridin-2-yl)cyclopropanecarboxamide.

Workup

  1. stirringthe mixture was stirred for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate (30 mL×3)
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0134907fbf7b4ce1b82a29fc8016fdff
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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