4-Methylmorpholine → N-(2-aminophenyl)-6-[(3-methoxyphenoxy)acetyl]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxamide

HRID 2093103Notes

Reaction equation

HRID 2093103 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH2:7][C:8]([OH:10])=O.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.CN1CCOCC1.[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[NH:49][C:50]([C:52]1[S:60][C:55]2[CH2:56][NH:57][CH2:58][CH2:59][C:54]=2[CH:53]=1)=[O:51]>CN(C=O)C>[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[NH:49][C:50]([C:52]1[S:60][C:55]2[CH2:56][N:57]([C:8](=[O:10])[CH2:7][O:6][C:5]3[CH:11]=[CH:12][CH:13]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:58][CH2:59][C:54]=2[CH:53]=1)=[O:51]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 749692-(3-Methoxyphenoxy)acetic acidHCID 757711-HydroxybenzotriazoleHCID 58117017N-(2-aminophenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxamide

Product 1

HCID 25230273N-(2-aminophenyl)-6-[(3-methoxyphenoxy)acetyl]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of (3-Methoxy-phenoxy)-acetic acid (1.0 mmol) in dry DMF (10 mL), were added 1-hydroxybenzotriazole (1.2 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (2 mmol) and N-methylmorpholine (2.0 mmol). Solution was cooled to 0° C. N-(2-aminophenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxamide (1.0 eq) obtained in step VII of example 216 was then added and mixture was stirred at room temperature overnight.

Sources & evidence

ORD record
ord-3049a59f7eeb437582f87092e7118c7c
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

Loading…