Acetic Acid → N-[2-(S)-(3,4-Dichlorophenyl)-4-[4[(R)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-methyl-3-cyano-1-naphthamide Citrate Hydrate

HRID 840409Notes

Reaction equation

HRID 840409 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([O-:8])(=[O:7])[CH3:6].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([C@H:18]([CH2:36][CH:37]=O)[CH2:19][N:20]([CH3:35])[C:21]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[C:25]([C:33]#[N:34])[CH:24]=2)=[O:22])[CH:14]=[CH:15][C:16]=1[Cl:17].[CH3:39][S@:40]([C:42]1C=C[CH:45]=[CH:44][C:43]=1C1CCNCC1)=[O:41].[NH:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55]1.[C:60]([OH:63])(=[O:62])[CH3:61]>CCOCC>[OH2:3].[C:60]([OH:63])(=[O:62])[CH2:61][C:2]([CH2:6][C:5]([OH:8])=[O:7])([C:1]([OH:4])=[O:3])[OH:22].[Cl:10][C:11]1[CH:12]=[C:13]([C@H:18]([CH2:36][CH2:37][N:54]2[CH2:59][CH2:58][CH:57]([C:1]3[CH:2]=[CH:45][CH:44]=[CH:43][C:42]=3[S@@:40]([CH3:39])=[O:41])[CH2:56][CH2:55]2)[CH2:19][N:20]([CH3:35])[C:21]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[C:25]([C:33]#[N:34])[CH:24]=2)=[O:22])[CH:14]=[CH:15][C:16]=1[Cl:17]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 187156453-Cyano-N-[(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl)-N-methyl-1-naphthamideHCID 23662384Sodium DiacetateHCID 538345584-[(R)-2-methylsulfinylphenyl]-piperidine

Product 1

HCID 70157809N-[2-(S)-(3,4-Dichlorophenyl)-4-[4[(R)-2-methylsulfinylphenyl]-1-piperidinyl]butyl]-N-methyl-3-cyano-1-naphthamide Citrate Hydrate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using standard reductive amination conditions (except that acetic acid-sodium acetate buffer was substituted for acetic acid) N-[(S)-2-(3,4-dichlorophenyl)-4-oxobutyl]-N-methyl-3-cyano-1-naphthamide (468 mg, 1.1 mmol) was reacted with 4-[(R)-2-methylsulfinylphenyl]-piperidine (piperidine (Shenvi, A B; Jacobs, R T; Miller, S C; Ohnmacht. C J Jr; Veale, C A.; WO 9516682) (232 mg, 1.04 mmol), converted to the citrate salt, and isolated by filtration from Et2O to afford the title compound (651.2 mg) as a white powder. MS m/z 632 (M+H); analysis for C35H35Cl2N3O2S .C6H8O7.H2O: calculated: C, 58.43; H, 5.38; N, 4.98; found: C, 58.10; H, 5.20; N. 4.82.

Sources & evidence

ORD record
ord-f044b248004e464d9b4d60ca8248645e
Source dataset
uspto-grants-2002_04
Patent number
US06365602B1

Reaction notes

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