3-(4-Aminophenyl)-1,4-dimethylpiperazin-2-one → HCID 66711745, compound

HRID 1262238Notes

Reaction equation

HRID 1262238 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[N:37]([CH3:38])[CH2:36][CH2:35][N:34]([CH3:39])[C:33]2=[O:40])=[CH:28][CH:27]=1>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21]([NH:25][C:26]4[CH:27]=[CH:28][C:29]([CH:32]5[C:33](=[O:40])[N:34]([CH3:39])[CH2:35][CH2:36][N:37]5[CH3:38])=[CH:30][CH:31]=4)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:7])=[O:8])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 576251203-(4-Aminophenyl)-1,4-dimethylpiperazin-2-oneHCID 178449976HCID 178449976, compound

Product 1

HCID 66711745HCID 66711745, compound

Procedure

N-tert-Butyl-3-{2-[4-(1,4-dimethyl-3-oxo-piperazin-2-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-benzenesulfonamide was prepared from N-tert-butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide and 3-(4-amino-phenyl)-1,4-dimethyl-piperazin-2-one in an analogous manner to Example 1052a. Product isolated as an orange foam (90 mg, 56%). LCMS (m/e) 548 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.97 (s, 1H), 8.74 (s, 1H), 8.21 (d, 1H, J=7.9 Hz), 7.89 (d, 1H, J=7.8 Hz), 7.64-7.54 (m, 3H), 7.42 (d, 2H, J=8.3 Hz), 7.10 (d, 1H, J=4.8 Hz), 6.91-6.83 (m, 2H), 4.86 (s, 1H), 3.83-3.70 (m, 2H), 3.27-3.17 (m, 1H), 3.04 (s, 3H), 3.06-2.98 (m, 1H), 2.75-2.65 (m, 1H), 2.21 (s, 3H), 1.14 (s, 9H).

Sources & evidence

ORD record
ord-df95e86659974167a0a0b42b0e050c87
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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