Dimethylformamide → HCID 86646061, compound

HRID 2366772Notes

Reaction equation

HRID 2366772 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. This is reaction mixture was added to a solution of 5-chloro[1,3]thiazolo[5,4-b]pyridin-2-amine (185 mg, 1.00 mmol) in tetrahydrofuran (10 mL) at 0° C., and the mixture was stirred for 2 hr. Water (10 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (30 mLx3). 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. customThis is reaction mixture
  2. stirringthe mixture was stirred for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate (30 mLx3)
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-23e1b475b03c4d0d881dc12df96caed1
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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