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

HRID 1171316Notes

Reaction equation

HRID 1171316 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].[CH3:38][O:39][CH:40]([O:44][CH3:45])[CH2:41][NH:42][CH3:43]>>[CH3:38][O:39][CH:40]([O:44][CH3:45])[CH2:41][N:42]([CH3:43])[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 85032,2-DimethoxyethylmethylamineHCID 667379693-fluoro-N-[4-(2-methanesulfonyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-5-piperidin-1-yl-benzamide

Product 1

HCID 59553379N-[4-({2-[(2,2-Dimethoxyethyl)(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 (2,2-dimethoxy-ethyl)-methylamine according to conditions described in general procedure C. Mp: 135-136° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.59-1.61 (m, 6 H), 2.82 (s, 3 H), 3.01-3.08 (m, 2 H), 3.27-3.30 (m, 10 H), 3.60 (s, 1 H), 6.25-6.40 (bd, 1H), 6.93-6.98 (m, 1H), 7.16 (d, J=8.5 Hz, 1 H), 7.40 (d, J=9.0 Hz, 1 H), 7.45 (s, 1 H), 7.54-7.59 (m, 3 H), 7.80 (s, 1 H), 7.96-7.99 (m, 1 H), 8.27 (d, J=4.4 Hz, 1 H), 10.41 (s, 1 H).

Sources & evidence

ORD record
ord-4572f9ef6cd649ce8af677433c154fe8
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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