HCID 66712498, compound → HCID 66712278, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([C:42]2[N:50]3[C:45]([CH:46]=[N:47][C:48](O)=[N:49]3)=[CH:44][CH:43]=2)[CH:37]=1)(=[O:35])=[O:34])([CH3:31])([CH3:30])[CH3:29]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:48]2[N:47]=[CH:46][C:45]3=[CH:44][CH:43]=[C:42]([C:38]4[CH:39]=[CH:40][CH:41]=[C:36]([S:33](=[O:35])(=[O:34])[NH:32][C:28]([CH3:29])([CH3:31])[CH3:30])[CH:37]=4)[N:50]3[N:49]=2)=[CH:23][CH:22]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
Procedure
Analogous to Example 1510b, 2-(4-Amino-phenyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.180 g, 0.477 mmol) and N-tert-Butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (149 mg, 0.429 mmol) were reacted to afford 2-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperazine-1,4-dicarboxylic acid di-tert-butyl ester, which was treated with 10% TFA in dichloromethane overnight. Conc. and purification by HPLC afforded N-tert-Butyl-3-[2-(4-piperazin-2-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzenesulfonamide as the TFA salt (162 mg, 61%). LCMS (HPLC): 0.8 min, m/z=506 (M+H); 1H-NMR (DMSO-d6): 9.81 (s, 1H), 9.44 (br s, 3H), 9.09 (s, 1H), 8.57 (s, 1H), 8.34 (d, 1H, J=8.0 Hz), 7.87 (m, 3H), 7.74 (m, 1H), 7.62 (s, 1H), 7.48 (d, 2H, J=8.5 Hz), 7.24 (d, 1H, J=4.8 Hz), 7.05 (d, 1H, J=4.8 Hz), 4.46 (m, 1H), 3.59 (m, 3H), 3.27 (m, 3H), 1.11 (s, 9H).
Sources & evidence
- ORD record
- ord-00b69200b7564011b3f555d9341805ee
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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