4,4-Difluoropiperidine → N-(4-{[2-(4,4-Difluoropiperidin-1-yl)pyrimidin-4-yl]oxy}-1-naphthyl)-3-fluoro-5-piperidin-1-ylbenzamide

HRID 1641215Notes

Reaction equation

HRID 1641215 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[F:38][C:39]1([F:45])[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>>[F:38][C:39]1([F:45])[CH2:44][CH2:43][N:42]([C:21]2[N:20]=[C:19]([O:18][C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]([NH:7][C:5](=[O:6])[C:4]4[CH:29]=[C:30]([N:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)[CH:31]=[C:2]([F:1])[CH:3]=4)=[CH:9][CH:10]=3)[CH:24]=[CH:23][N:22]=2)[CH2:41][CH2:40]1

Participants

3

Reactant 2

HCID 27583524,4-DifluoropiperidineHCID 667379693-fluoro-N-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide

Product 1

HCID 59553087N-(4-{[2-(4,4-Difluoropiperidin-1-yl)pyrimidin-4-yl]oxy}-1-naphthyl)-3-fluoro-5-piperidin-1-ylbenzamide

Procedure

Compound is prepared from 3-fluoro-N-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide and 4,4-difluoropiperidine according to conditions described in general procedure C. Mp: 172-174° C.; 1H NMR (400 MHz, CDCl3) δ 1.63-1.71 (m, 6 H), 1.86-1.91 (m, 4 H), 3.28 (t, J=5.8 Hz, 4 H), 3.77 (s, 4 H), 6.07 (d, J=5.8 Hz, 1 H), 6.75-6.79 (m, 1 H), 6.98 (d, J=8.0 Hz, 1 H), 7.29-7.31 (m, 2 H), 7.49-7.60 (m, 2 H), 7.90-7.99 (m, 3 H), 8.12 (s, 1 H), 8.17 (d, J=5.5 Hz, 1 H).

Sources & evidence

ORD record
ord-cda0caf6378d4cf48cab3fbb6f3b2be9
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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