4-Morpholinecarbonyl chloride → Trifluoro-methanesulfonic acid 7-{[1-(morpholine-4-carbonyl)-piperidin-4-ylmethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-yl ester

HRID 1168889Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][N:8]([CH2:27][CH2:28][CH3:29])[CH:9]2[CH2:18][C:17]3[CH:16]=[C:15]([O:19][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:22])=[O:21])[CH:14]=[CH:13][C:12]=3[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.[N:30]1([C:36](Cl)=[O:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C(#N)C.ClCCl.CCN(C(C)C)C(C)C>[N:30]1([C:36]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][N:8]([CH2:27][CH2:28][CH3:29])[CH:9]3[CH2:18][C:17]4[CH:16]=[C:15]([O:19][S:20]([C:23]([F:26])([F:24])[F:25])(=[O:22])=[O:21])[CH:14]=[CH:13][C:12]=4[CH2:11][CH2:10]3)[CH2:3][CH2:2]2)=[O:37])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 7-(piperidin-4-ylmethyl-propyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl ester (200 μL of a 0.19 M solution in acetonitrile, 36 μmole) was added 220 μL of a 0.25 M solution of morpholine 4-carbonyl chloride in dichloromethane and 30 μL of DIEA. The solution was allowed to stir for 48 h at 25° C. under N2, and was then concentrated in vacuo. The final product was isolated by preparative RPHPLC (YMC Combiprep ODS-A column, 10-90% acetonitrile: water (0.1% TFA)) to afford trifluoro-methanesulfonic acid 7-{[1-(morpholine-4-carbonyl)-piperidin-4-ylmethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-yl ester (12.8 mg) 106[M+H]+=548.

Workup

concentrationwas then concentrated in vacuo

Sources & evidence

ORD record: ord-29b12de3e30241e0bc63a1348a2dc3c1
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06627644B2

Reaction notes

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