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

HRID 983473Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([N:12]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[O:24])[CH2:19][CH2:18]3)[CH2:13][CH2:14][CH3:15])[CH2:9]2)=[CH:4][CH:3]=1.[C:31](Cl)(=[O:35])[CH:32]([CH3:34])[CH3:33]>ClCCl.CCN(C(C)C)C(C)C>[N:25]1([C:23]([N:20]2[CH2:19][CH2:18][CH:17]([CH2:16][N:12]([CH2:13][CH2:14][CH3:15])[CH:8]3[CH2:9][C:10]4[CH:11]=[C:2]([NH:1][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])[CH:3]=[CH:4][C:5]=4[CH2:6][CH2:7]3)[CH2:22][CH2:21]2)=[O:24])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (4-{[(7-amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidin-1-yl)-morpholin-4-yl-methanone (200 μL of 0.25 M in dichloromethane, 50 μmol ) 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-(morpholine-4-carbonyl)-piperidin-4-ylmethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-yl)-isobutyramide (8.6 mg) 96, [M+H]+=485.

Workup

concentrationwas then concentrated in vacuo

Sources & evidence

ORD record: ord-4daf2b0d52fc4074bbe8e1a25db77517
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864266B2

Reaction notes

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