4-Chloroaniline → {4-[(4-Chloro-phenyl)-(2-methyl-thiazol-4-ylmethyl)-amino]-4'-methyl-[1,4']bipiperidinyl-1'-yl}-(2,4-dimethyl-pyridin-3-yl)-methanone

HRID 748481Notes

Reaction equation

HRID 748481 reaction equation
[CH3:1][C:2]1([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]3[N:17]=[C:18]([CH3:21])[S:19][CH:20]=3)[CH2:10][CH2:9]2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:22][C:23]1[N:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:24]=1[C:25]([OH:27])=O.CC1(N2CCC(N(C3C=CC=CC=3)C3C=NC=CC=3)CC2)CCNCC1.[Cl:59][C:60]1[CH:65]=[CH:64][C:63](N)=[CH:62][CH:61]=1.C(OC(N1CCC(=O)CC1)=O)(C)(C)C.ClCC1N=C(C)SC=1>>[Cl:59][C:60]1[CH:65]=[CH:64][C:63]([N:14]([CH2:15][C:16]2[N:17]=[C:18]([CH3:21])[S:19][CH:20]=2)[CH:11]2[CH2:10][CH2:9][N:8]([C:2]3([CH3:1])[CH2:3][CH2:4][N:5]([C:25]([C:24]4[C:23]([CH3:22])=[N:31][CH:30]=[CH:29][C:28]=4[CH3:32])=[O:27])[CH2:6][CH2:7]3)[CH2:13][CH2:12]2)=[CH:62][CH:61]=1

Participants

7

Reactant 6

HCID 78124-ChloroanilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazoleHCID 15125612,4-Dimethyl-3-pyridinecarboxylic acidHCID 69024358(4'-Methyl-[1,4']bipiperidinyl-4-yl)-phenyl-pyridin-3-yl-amineHCID 866024624'-Methyl-[1,4']bipiperidinyl-4-yl-(2-methyl-thiazol-4-ylmethyl)-amine

Product 1

HCID 59750630{4-[(4-Chloro-phenyl)-(2-methyl-thiazol-4-ylmethyl)-amino]-4'-methyl-[1,4']bipiperidinyl-1'-yl}-(2,4-dimethyl-pyridin-3-yl)-methanone

Procedure

It is prepared from (chloro-phenyl)-(4′-methyl-[1,4′]bipiperidinyl-4-yl-(2-methyl-thiazol-4-ylmethyl)-amine and 2,4-dimethyl-nicotinic acid using a procedure as described in Example 1 of PCT/EP02/03871. MS-ESI 552 [M+H]+. (4′-Methyl-[1,4′]bipiperidinyl-4-yl)-phenyl-pyridin-3-yl-amine used as starting material can be prepared from 4-chloro-phenylamine, 4-oxo-piperidine-1-carboxylic acid tert-butyl ester and 4-chloromethyl-2-methyl-thiazole using procedures as described in Example 51e, 52, 1b, 1c and 1d of PCT/EP02/03871. MS/ESI 419 [M+H]+

Sources & evidence

ORD record
ord-99ac31a605254886a0a947ebe4d4a0fa
Source dataset
uspto-grants-2008_07
Patent number
US07399771B2

Reaction notes

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