2-Fluoroethyl bromide → 2-{5-Chloro-2-[10-(2-fluoro-ethyl)-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamide
Reaction equation
[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=2[C:28]([NH:30][CH3:31])=[O:29])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]3[C:17](=[CH:18][CH:19]=2)[CH:16]2[CH2:20][CH2:21][CH:12]3[CH2:13][N:14]([CH2:22][C:23]#C)[CH2:15]2)=[N:6][CH:7]=1.BrCC[F:39]>>[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=2[C:28]([NH:30][CH3:31])=[O:29])=[N:4][C:5]([NH:8][C:9]2[CH:10]=[C:11]3[C:17](=[CH:18][CH:19]=2)[CH:16]2[CH2:20][CH2:21][CH:12]3[CH2:13][N:14]([CH2:22][CH2:23][F:39])[CH2:15]2)=[N:6][CH:7]=1Participants
Reactant 2
Product 1
Procedure
2-{5-Chloro-2-[10-(2-fluoro-ethyl)-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamide was prepared from 2-[5-chloro-2-(10-prop-2-ynyl-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide and 1-bromo-2-fluoro-ethane in an analogous manner to Example 279. Product isolated as a yellow oil (22 mg, 66%). LCMS (m/e) 495 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 11.03 (s, 1H), 8.65 (d, 1H, J=8.4 Hz), 8.08 (s, 1H), 7.50-7.45 (m, 1H), 7.45-7.39 (m, 1H), 7.36 (d, 1H, J=2.2 Hz), 7.30-7.20 (m, 1H), 7.10-6.95 (m, 3H), 6.53 (bs, 1H), 4.52 (dt, 2H, J=5.1 and 47.7 Hz), 3.02 (d, 3H, J=4.8 Hz), 3.02-2.93 (m, 3H), 2.93-2.89 (m, 1H), 2.74 (dt, 2H, J=5.1 and 27.3 Hz), 2.43-2.31 (m, 2H), 2.27-2.18 (m, 2H), 1.67-1.57 (m, 2H).
Sources & evidence
- ORD record
- ord-3c5c8c1819a54b6eb9a7bb5651071ea5
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
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