4-(4-methylpiperazine-1-carbonyl)benzoic Acid → 1-(4-(6-((Dimethylamino)methyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-2-yl)phenyl)-3-(4-(4-methylpiperazine-1-carbonyl)phenyl)urea

HRID 63795Notes

Reaction equation

HRID 63795 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[CH:18]=[CH:17][C:13](C(O)=O)=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.CN1CC[N:23]([C:26](C2C=CC(C(N=[N+]=[N-])=O)=CC=2)=[O:27])CC1.[NH2:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[N:51]=[C:50]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)[C:49]3=[CH:58][C:59]([CH2:61][N:62]([CH3:64])[CH3:63])=[CH:60][N:48]3[N:47]=2)=[CH:42][CH:41]=1>>[CH3:63][N:62]([CH2:61][C:59]1[CH:58]=[C:49]2[N:48]([CH:60]=1)[N:47]=[C:46]([C:43]1[CH:44]=[CH:45][C:40]([NH:39][C:26]([NH:23][C:13]3[CH:12]=[CH:11][C:10]([C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)=[O:9])=[CH:18][CH:17]=3)=[O:27])=[CH:41][CH:42]=1)[N:51]=[C:50]2[N:52]1[CH2:53][CH2:54][O:55][CH2:56][CH2:57]1)[CH3:64]

Participants

4

Reactant 3

HCID 20514174-(4-methylpiperazine-1-carbonyl)benzoic AcidHCID 117987912HCID 117987912, compoundHCID 117988374HCID 117988374, compound

Product 1

HCID 725491041-(4-(6-((Dimethylamino)methyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-2-yl)phenyl)-3-(4-(4-methylpiperazine-1-carbonyl)phenyl)ureaYield 15.1%

Procedure

According to the general methods described in example 13, 4-(4-methylpiperazine-1-carbonyl)benzoic acid was used as starting material, and the resulting 4-(4-methylpiperazine-1-carbonyl)benzoyl azide reacted with 13a to give a white solid (9 mg, 15.1%). 1H NMR (300 MHz, DMSO-d6): δ 9.63 (br, s, 2H), 8.16 (d, J=8.9 Hz, 2H), 7.92 (s, 1H), 7.57 (d, J=8.9 Hz, 2H), 7.53 (d, J=8.5 Hz, 2H), 7.34 (d, J=8.5 Hz, 2H), 7.13 (s, 1H), 4.07 (br, s, 6H), 3.80 (br, s, 4H), 3.51 (br, s, 4H), 3.06 (br s, 2H), 2.55 (s, 6H), 2.38 (br s, 2H), 2.24 (s, 3H). ESI-MS: 598 (M+1).

Sources & evidence

ORD record
ord-74cbe61f66974864af3f503e3f73580d
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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