1-Amino-1-methylurea → 1-methyl-1-[(E)-1-[3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]urea
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]3[N:16]4[N:17]=[C:18]([C:21](=O)[CH3:22])[CH:19]=[CH:20][C:15]4=[N:14][N:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:24][N:25]([C:27]([NH2:29])=[O:28])[NH2:26].N1C2C(=CC(CC3N4N=C(/C(=N/NC(N)=O)/C)C=CC4=NN=3)=CC=2)C=CC=1>>[CH3:24][N:25]([C:27]([NH2:29])=[O:28])/[N:26]=[C:21](/[C:18]1[CH:19]=[CH:20][C:15]2[N:16]([C:12]([CH2:11][C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:1]=[CH:2][CH:3]=[CH:4]4)=[N:13][N:14]=2)[N:17]=1)\[CH3:22]Participants
4
Reactant 3
Product 1
Procedure
The title compound (27 mg, 55%) was synthesized from 1-(3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (40 mg, 0.132 mmol) and 1-methylhydrazine-carboxamide (23.5 mg, 0.264 mmol) using the same procedure as described in the synthesis of 37. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.06 (d, 1H), 8.73 (d, 1H), 8.17 (m, 4H), 8.00 (d, 1H), 7.79 (m, 1H), 6.69 (s, 2H), 4.82 (s, 2H), 3.27 (s, 3H), 2.32 (s, 3H). LCMS (method A): [MH]+=375.0, tR=3.79 min.
Sources & evidence
- ORD record
- ord-620f2ef728e84e6190efe3eaf14df08a
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497368B2
Reaction notes
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