Morpholine → Morpholine-4-carboxylic acid (7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-amide

HRID 917435Notes

Reaction equation

HRID 917435 reaction equation
C1(O[C:8](=[O:27])[NH:9][C:10]2[S:11][C:12]3[C:13]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[N:14][CH:15]=[C:16]([O:19][CH3:20])[C:17]=3[N:18]=2)C=CC=CC=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>ClC(Cl)C.O1CCCC1>[CH3:20][O:19][C:16]1[C:17]2[N:18]=[C:10]([NH:9][C:8]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])[S:11][C:12]=2[C:13]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86597258(7-Methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-carbamic acid phenyl ester

Product 1

HCID 86597259Morpholine-4-carboxylic acid (7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-amideYield 34%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 145 mg (0.38 mmol) (7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-carbamic acid phenyl ester in 6 ml dichloroethane and 2 ml tetrahydrofuran at room temperature was added 0.16 ml (1.88 mmol) morpholine and stirring continued at 50° C. for 16 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) followed by trituration in ether afforded 48 mg (34%) morpholine-4-carboxylic acid (7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-amide as a white crystalline solid. ES-MS m/e (%): 380 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-1b6efe3b31b34eacaa1eb55d95b6a8db
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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