3-(3-Aminophenyl)-1,4-dimethylpiperazin-2-one → 1,4-Dimethyl-3-(3-{7-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-piperazin-2-one

HRID 1262244Notes

Reaction equation

HRID 1262244 reaction equation
[N:1]1([S:6]([C:9]2[CH:10]=[C:11]([C:15]3[N:23]4[C:18]([CH:19]=[N:20][C:21](O)=[N:22]4)=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:25][C:26]1[CH:27]=[C:28]([CH:32]2[N:37]([CH3:38])[CH2:36][CH2:35][N:34]([CH3:39])[C:33]2=[O:40])[CH:29]=[CH:30][CH:31]=1>>[CH3:39][N:34]1[CH2:35][CH2:36][N:37]([CH3:38])[CH:32]([C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([NH:25][C:21]3[N:20]=[CH:19][C:18]4=[CH:17][CH:16]=[C:15]([C:11]5[CH:12]=[CH:13][CH:14]=[C:9]([S:6]([N:1]6[CH2:2][CH2:3][CH2:4][CH2:5]6)(=[O:8])=[O:7])[CH:10]=5)[N:23]4[N:22]=3)[CH:27]=2)[C:33]1=[O:40]

Participants

3

Reactant 2

HCID 574160813-(3-Aminophenyl)-1,4-dimethylpiperazin-2-oneHCID 1785273247-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ol

Product 1

HCID 667123671,4-Dimethyl-3-(3-{7-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-piperazin-2-one

Procedure

1,4-Dimethyl-3-(3-{7-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-piperazin-2-one was prepared from 7-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ol and 3-(3-amino-phenyl)-1,4-dimethyl-piperazin-2-one in an analogous manner to Example 1052a. Product isolated as an orange foam (82 mg, 49%). LCMS (m/e) 546 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.75 (s, 1H), 8.65 (d, 1H, J=8.2 Hz), 8.31 (s, 1H), 7.87-7.77 (m, 2H), 7.70-7.62 (m, 1H), 7.41-7.32 (m, 2H), 7.12-7.03 (m, 2H), 6.94 (s, 1H), 6.85 (d, 1H, J=4.7 Hz), 3.78-3.65 (m, 2H), 3.34-3.25 (m, 4H), 3.25-3.15 (m, 1H), 3.70-2.96 (m, 1H), 2.99 (s, 3H), 2.74-2.62 (m, 1H), 2.18 (s, 3H), 1.82-1.72 (m, 4H).

Sources & evidence

ORD record
ord-756ea1b516c342f598c2bdb8a535d297
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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