2-Chlorobenzenesulfonyl chloride → 2-Chloro-benzenesulfonic acid 7-{[1-(morpholine-4-carbonyl)-piperidin-4-yl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-yl ester

HRID 393214Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([N:12]([CH2:27][CH2:28][CH3:29])[CH:13]3[CH2:18][CH2:17][N:16]([C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:20])[CH2:15][CH2:14]3)[CH2:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[S:46](Cl)(=[O:48])=[O:47]>C1COCC1>[N:21]1([C:19]([N:16]2[CH2:15][CH2:14][CH:13]([N:12]([CH2:27][CH2:28][CH3:29])[CH:8]3[CH2:9][C:10]4[CH:11]=[C:2]([O:1][S:46]([C:41]5[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=5[Cl:39])(=[O:48])=[O:47])[CH:3]=[CH:4][C:5]=4[CH2:6][CH2:7]3)[CH2:18][CH2:17]2)=[O:20])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of {4-[(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidin-1-yl}-morpholin-4-yl-methanone (50 μmole in 420 μL DCM) was added 30 μL of DIEA followed by 220 μL of a 0.25M solution of 2-chlorobenzenesulfonyl chloride in THF. The solution was allowed to stir for 24 h at 25° C. under N2. 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 2-Chloro-benzenesulfonic acid 7-{[1-(morpholine4-carbonyl)-piperidin-4-yl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-yl ester 40 (5.1 mg), [M+H]+=690.

Workup

concentrationConcentrated in vacuo

Sources & evidence

ORD record: ord-3a3f9b0807804c0caab93e561e7f0d32
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806278B2

Reaction notes

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