5,6,7,8-Tetrahydronaphthalene-1-carbonyl chloride → N-[(S)-2-(3,4-Dichlorophenyl)-4-[4-[tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1-piperidinyl]butyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide

HRID 2185874Notes

Reaction equation

HRID 2185874 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:26][CH2:25][CH2:24][NH:23][C:22]3=[O:27])[CH2:17][CH2:16]2)[CH2:10][NH:11][CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:28]1([C:38](Cl)=[O:39])[C:37]2[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=2[CH:31]=[CH:30][CH:29]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[CH2:26][CH2:25][CH2:24][NH:23][C:22]3=[O:27])[CH2:17][CH2:16]2)[CH2:10][N:11]([CH3:12])[C:38]([C:28]2[C:37]3[CH2:36][CH2:35][CH2:34][CH2:33][C:32]=3[CH:31]=[CH:30][CH:29]=2)=[O:39])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 27531625,6,7,8-Tetrahydronaphthalene-1-carbonyl chlorideHCID 11464101N-[(S)-2-(3,4-dichlorophenyl)4-[4-[tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1-piperidinyl]butyl]-N-methylamine

Product 1

HCID 70160988N-[(S)-2-(3,4-Dichlorophenyl)-4-[4-[tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1-piperidinyl]butyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide

Procedure

Using standard acylation conditions N-[(S)-2-(3,4-dichlorophenyl)4-[4-[tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1-piperidinyl]butyl]-N-methylamine (S. C. Miller,. WO 9505377) was reacted with 5,6,7,8-tetrahydro-1-naphthalenecarbonyl chloride (Example 1) and the product was converted to the citrate salt MS: m/z 571 (M+H). Analysis for C31H40O2Cl2N4.C6H8O7.3.0H2O: calculated: C,54.34; H, 6.66; N, 6.85; found: C, 54.26; H, 5.97; N, 6.47.

Sources & evidence

ORD record
ord-3b3d3f3771f2434896df718cb8264469
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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