Isobutyryl chloride → N-{7-[(1-methanesulfonyl-piperidin-4-ylmethyl)-propyl-amino]-5,6,7,8-tetrahydro-naphthalen-2-yl}-isobutyramide

HRID 983470Notes

Reaction equation

[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]([CH2:24][CH2:25][CH3:26])[CH:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][C:17]([NH2:23])=[CH:18][CH:19]=3)[CH2:14]2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[C:27](Cl)(=[O:31])[CH:28]([CH3:30])[CH3:29]>ClCCl.CCN(C(C)C)C(C)C>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][N:12]([CH2:24][CH2:25][CH3:26])[CH:13]2[CH2:14][C:15]3[CH:16]=[C:17]([NH:23][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH:18]=[CH:19][C:20]=3[CH2:21][CH2:22]2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of N-(1-methanesulfonyl-piperidin-4-ylmethyl)-N-propyl-1,2,3,4-tetrahydro-naphthalene-2,7-diamine (200 μL of a 0.25 M solution in dichloromethane, 50 μmole) was added 220 μL of a 0.25 M solution of isobutyryl chloride in dichloromethane and 30 μL of DIEA. The solution was allowed to stir for 72 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 N-{7-[(1-methanesulfonyl-piperidin-4-ylmethyl)-propyl-amino]-5,6,7,8-tetrahydro-naphthalen-2-yl}-isobutyramide (10.4 mg) 86, [M+H]+=450.

Workup

concentrationwas then concentrated in vacuo

Sources & evidence

ORD record: ord-669f165dd96d49bfbcefdf45aa5a05a6
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864266B2

Reaction notes

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