6-(3-Fluorophenyl)-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-3-pyridinecarboxamide → N,2'-Dimethyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-3,4'-bipyridine-6-carboxamide

HRID 534805Notes

Reaction equation

HRID 534805 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:31])[C:16]([C:18]3[N:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([CH3:30])[CH:25]=4)=[CH:20][CH:19]=3)=[O:17])=[CH:11][CH:10]=2)[CH2:5][CH2:4][N:3]1C(OC(C)(C)C)=O.FC1C=C(C2N=CC(C(N(C)C3C=CC(CN4CCN[C@@H](C)C4)=CC=3)=O)=CC=2)C=CC=1>C(Cl)Cl.CO>[CH3:31][N:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:6]2[CH2:5][CH2:4][NH:3][C@@H:2]([CH3:1])[CH2:7]2)=[CH:14][CH:13]=1)[C:16]([C:18]1[N:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([CH3:30])[CH:25]=2)=[CH:20][CH:19]=1)=[O:17]

Participants

4

Reactant 2

HCID 237290226-(3-Fluorophenyl)-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-3-pyridinecarboxamideHCID 592621681,1-dimethylethyl (2S)-2-methyl-4-[(4-{methyl[(2'-methyl-3,4'-bipyridin-6-yl)carbonyl]amino}phenyl)methyl]-1-piperazinecarboxylate

Product 1

HCID 23728873N,2'-Dimethyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-3,4'-bipyridine-6-carboxamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from 1,1-dimethylethyl (2S)-2-methyl-4-[(4-{methyl[(2′-methyl-3,4′-bipyridin-6-yl)carbonyl]amino}phenyl)methyl]-1-piperazinecarboxylate (D130) using a procedure similar to that described for E1 in Example 1 although hydrochloride salt preparation was carried out in DCM/MeOH (1:1). δH (MeOD, 400 MHz) 8.96 (1H, br.m), 8.76 (1H, d), 8.39 (1H, br.m), 8.33 (1H, s), 8.23 (1H, d), 7.81 (1H, br.d), 7.58 (2H, br.s), 7.36 (2H, br.s), 3.86 (1H, br.s), 3.58-3.71 (4H, m), 3.54 (3H, s), 3.44 (1H, m), 3.34 (2H, s), 3.30 (1H, m), 2.85 (3H, s), 1.40 (3H, d), NH not observed. MS (ES+): 316.1, no molecular ion (MH+) observed.

Sources & evidence

ORD record
ord-738357709d624d668fc33708e13934ab
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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