1,3-Dioxolane-2-methanamine, N-methyl- → N-[4-({2-[(1,3-Dioxolan-2-ylmethyl)(methyl)amino]pyrimidin-4-yl}oxy)-1-naphthyl]-3-fluoro-5-piperidin-1-ylbenzamide

HRID 1171344Notes

Reaction equation

HRID 1171344 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].[O:38]1[CH2:42][CH2:41][O:40][CH:39]1[CH2:43][NH:44][CH3:45]>>[O:38]1[CH2:42][CH2:41][O:40][CH:39]1[CH2:43][N:44]([CH3:45])[C:21]1[N:20]=[C:19]([O:18][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:29]=[C:30]([N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)[CH:31]=[C:2]([F:1])[CH:3]=3)=[CH:9][CH:10]=2)[CH:24]=[CH:23][N:22]=1

Participants

3

Reactant 2

HCID 5417541,3-Dioxolane-2-methanamine, N-methyl-HCID 667379693-fluoro-N-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide

Product 1

HCID 59553326N-[4-({2-[(1,3-Dioxolan-2-ylmethyl)(methyl)amino]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 [1,3]dioxolan-2-ylmethylmethylamine according to conditions described in general procedure C. Mp: 125-127° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.57-1.61 (m, 6 H), 2.76 (bs, 1 H), 3.04 (bs, 1 H), 3.22-3.32 (m, 7 H), 3.55-3.86 (m, 4 H), 4.74-4.90 (m, 1 H), 6.26 (d, J=5.1 Hz, 1 H), 6.94-6.97 (m, 1 H), 7.15 (d, J=8.8 Hz, 1 H), 7.41 (d, J=8.0 Hz, 1 H), 7.46 (s, 1 H), 7.55-7.60 (m, 3 H), 7.82 (d, J=7.7 Hz, 1 H), 7.96-7.99 (m, 1 H), 8.24 (d, J=5.5 Hz, 1 H), 10.44 (s, 1 H).

Sources & evidence

ORD record
ord-c430140027be40569e03334cd3be066f
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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