3-Cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl)-N-methyl-1-naphthamide → N-[2-(S)-(3,4-Dichlorophenyl)-4-[4-[2-(methylsulfonyl)-4-methoxyphenyl]-1-piperidinyl]-butyl]-N-methyl-3-cyano-1-naphthamide Hydrochloride

HRID 840417Notes

Reaction equation

HRID 840417 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:27][CH:28]=O)[CH2:10][N:11]([CH3:26])[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]([C:24]#[N:25])[CH:15]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:30][S:31]([C:34]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=1[CH:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)(=[O:33])=[O:32]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:27][CH2:28][N:45]2[CH2:44][CH2:43][CH:42]([C:35]3[CH:36]=[CH:37][C:38]([O:40][CH3:41])=[CH:39][C:34]=3[S:31]([CH3:30])(=[O:33])=[O:32])[CH2:47][CH2:46]2)[CH2:10][N:11]([CH3:26])[C:12]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]([C:24]#[N:25])[CH:15]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 187156453-Cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl)-N-methyl-1-naphthamideHCID 226223344-(2-Methylsulfonyl-4-methoxyphenyl)piperidine

Product 1

HCID 18715621N-[2-(S)-(3,4-Dichlorophenyl)-4-[4-[2-(methylsulfonyl)-4-methoxyphenyl]-1-piperidinyl]-butyl]-N-methyl-3-cyano-1-naphthamide Hydrochloride

Procedure

Using standard reductive amination conditions N-[2-(S)-(3,4-dichlorophenyl)-4-oxobutyl]-N-methyl-3-cyano-1-naphthamide (0.130 g) was reacted with 4-(2-methylsulfonyl-4-methoxyphenyl)piperidine (0.082 g) and the product (0.074 g) was converted to the hydrochloride salt. MS m/z 678 (M+H). 1H NMR (DMSO-d6) δ 10.57 (m, 1H), 8.62 (m, 1H), 8.10 (m, 1H), 7.95-7.00 (m, 10H), 3.83 (s, 3H), 3.32 (s, 3H), 3.64-1.65 (m, 19H).

Sources & evidence

ORD record
ord-0252e0cc72e6406c8d3803d75bad39a8
Source dataset
uspto-grants-2002_04
Patent number
US06365602B1

Reaction notes

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