Pyridine → (7-Methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-carbamic acid phenyl ester

HRID 917434Notes

Reaction equation

HRID 917434 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:17]=[C:16]([NH2:18])[S:15][C:5]=2[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1.N1C=CC=CC=1.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27]>ClCCl.O1CCCC1>[C:29]1([O:28][C:26](=[O:27])[NH:18][C:16]2[S:15][C:5]3[C:6]([N:9]4[CH2:10][CH2:11][O:12][CH2:13][CH2:14]4)=[N:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=3[N:17]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 860385537-Methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-ylamine

Product 1

HCID 86597258(7-Methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-carbamic acid phenyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 500 mg (1.88 mmol) 7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-ylamine and 0.46 ml (5.63 mmol) pyridine in 15 ml dichloromethane and 5 ml tetrahydrofuran was added 0.28 ml (2.25 mmol) phenyl chloroformate and stirring continued at 50° C. for 3 h. The reaction mixture was then filtered and the filtrate concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) afforded 535 mg 74%) (7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-carbamic acid phenyl ester as a white solid. ES-MS m/e (%): 387 (M+H+, 100).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-92f1905cb81545099df8255090d23cb1
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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