Diisopropylethylamine → N-Methyl-N-(2-{2-[4-(1-methyl-piperidin-4-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenyl)-methanesulfonamide
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.CS([C:18]1[N:23]=[CH:22][C:21]2=[CH:24][CH:25]=[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:33]([CH3:38])[S:34]([CH3:37])(=[O:36])=[O:35])[N:20]2[N:19]=1)=O.C(N(CC)C(C)C)(C)C>>[CH3:38][N:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:26]1[N:20]2[C:21]([CH:22]=[N:23][C:18]([NH:14][C:11]3[CH:10]=[CH:9][C:8]([CH:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:13][CH:12]=3)=[N:19]2)=[CH:24][CH:25]=1)[S:34]([CH3:37])(=[O:35])=[O:36]Participants
Reactant 3
Product 1
Conditions
- Temperature
- 120 °C
Procedure
Into a 8-dram vial, 4-(1-Methyl-piperidin-4-yl)-phenylamine (0.115 g, 0.604 mmol), N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (0.100 g, 0.274 mmol), N,N-Diisopropylethylamine (0.1051 mL, 0.6036 mmol) and were added. The reaction was heated at 120° C. overnight. LCMS suggested presence of desired product. The solvent was removed under vacuum. The reaction mixture was purified via HPLC reverse phase chromatography with 0.1% TFA in Water and 0.1% TFA in ACN. The collected fractions were lyophilized to give N-Methyl-N-(2-{2-[4-(1-methyl-piperidin-4-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenyl)-methanesulfonamide as a yellow solid (38 mg, 36%). LCMS (E/I+) 491.16 (M+H). NMR 1H (DMSO-d6)-9.39 (s, 1H), 9.33 (s, 1H), 8.50 (d, 1H, J=7.59 Hz), 7.74 (d, 1H, J=7.59 Hz), 7.50-7.62 (m, 3H), 7.06 (d, 2H, J=7.59 Hz), 6.98 (bs, 1H), 6.93 (bs, 1H), 3.10 (s, 3H), 2.90 (s, 3H), 2.85 (d, 2H, J=11.43 Hz), 2.30-2.40 (m, 1H), 2.18 (s, 3H), 1.92 (t, 2H, J=11.43 Hz), 1.52-1.72 (m, 4H).
Sources & evidence
- ORD record
- ord-2d8ea50d3b324741884f4bd593c01380
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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