Methanol → HCID 58451271, compound

HRID 2366809Notes

Reaction equation

HRID 2366809 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2.[CH:30]1([C:33](Cl)=[O:34])[CH2:32][CH2:31]1.CO.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[CH:30]1([C:33]([NH:1][C:2]2[S:3][C:4]3[C:9]([N:10]=2)=[CH:8][CH:7]=[C:6]([O:11][C:12]2[CH:13]=[C:14]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH:15]=[CH:16][C:17]=2[CH3:18])[N:5]=3)=[O:34])[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 77637Cyclopropanecarbonyl chlorideHCID 86657978HCID 86657978, compound

Product 1

HCID 58451271HCID 58451271, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of benzyl {3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}carbamate (25.1 g, 61.9 mmol) in pyridine (200 mL) was added cyclopropanecarbonyl chloride (9.47 mL, 105 mmol) at 0° C., and the mixture was stirred at room temperature for 30 min. Methanol (100 mL) and potassium carbonate (8.55 g, 61.9 mmol) were added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The precipitated crystals were collected by filtration, and washed successively with methanol (200 mL), water (100 mL), methanol (100 mL) and hexane (100 mL) to give the title compound (23.9 g, 81%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed successively with methanol (200 mL), water (100 mL), methanol (100 mL) and hexane (100 mL)

Sources & evidence

ORD record
ord-a161b00b07aa41428369c3bcaf7d7867
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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