N-(2-Aminoethyl)piperidine → 3-Fluoro-5-piperidin-1-yl-N-[4-({2-[(2-piperidin-1-ylethyl)amino]pyrimidin-4-yl}oxy)-1-naphthyl]benzamide

HRID 1171341Notes

Reaction equation

HRID 1171341 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].[N:38]1([CH2:44][CH2:45][NH2:46])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[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]([NH:46][CH2:45][CH2:44][N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[N:20]=2)=[CH:10][CH:9]=1)=[O:6]

Participants

3

Reactant 2

HCID 33944N-(2-Aminoethyl)piperidineHCID 667379693-fluoro-N-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide

Product 1

HCID 595532103-Fluoro-5-piperidin-1-yl-N-[4-({2-[(2-piperidin-1-ylethyl)amino]pyrimidin-4-yl}oxy)-1-naphthyl]benzamide

Procedure

Compound is prepared from 3-fluoro-N-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide and 2-piperidin-1-yl-ethylamine according to conditions described in general procedure C. Mp: 88-89° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.31-1.39 (m, 6 H), 1.58-1.61 (m, 6 H), 1.99-2.27 (m, 6 H), 2.90-3.24 (m, 2 H), 3.23-3.29 (m, 4 H), 6.20-6.31 (bd, 1 H), 6.90-6.98 (m, 2 H), 7.15 (d, J=8.8 Hz, 1 H), 7.37 (d, J=8.0 Hz, 1 H), 7.43 (s, 1 H), 7.50-7.62 (m, 3 H), 7.78-7.80 (m, 1 H), 7.96 (d, J=8.0 Hz, 1 H), 8.20 (s 1 H), 10.40 (s, 1 H).

Sources & evidence

ORD record
ord-5eb5dc38cac5446c9a7df78df94bad72
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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