1-Pyrrolidineethanamine → 3-Fluoro-5-morpholin-4-yl-N-[4-({2-[(2-pyrrolidin-1-ylethyl)amino]pyrimidin-4-yl}oxy)-1-naphthyl]benzamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][O: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([CH2:43][CH2:44][NH2:45])[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][O: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:45][CH2:44][CH2:43][N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[N:20]=2)=[CH:10][CH:9]=1)=[O:6]Participants
3
Procedure
Compound is prepared from 3-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide and 2-pyrrolidin-1-yl-ethylamine according to conditions described in general procedure C. Mp: 95-97° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.59 (bs, 4 H), 2.08-2.2 (m, 2 H), 2.37-2.47 (m, 4 H), 2.92 (bs, 1 H), 3.23-3.25 (m, 5 H), 3.74 (t, J=4.4 Hz, 4 H), 6.32 (bd, 1 H), 6.59 (bs, 1 H), 7.04 (d, J=11.4 Hz, 1 H), 7.24 (d, J=8.8 Hz, 1 H), 7.38 (d, J=8.0 Hz, 1 H), 7.46 (s, 1 H), 7.53-7.58 (m, 3 H), 7.80 (d, J=6.6 Hz, 1 H), 7.98 (d, J=7.7 Hz, 1 H), 8.22 (s, 1 H), 10.43 (s, 1 H).
Sources & evidence
- ORD record
- ord-0e5161e9d18b47b8aed164955767e1f1
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08114873B2
Reaction notes
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