3-Amino-1-benzylthiourea → 1-benzyl-3-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]thiourea

HRID 456078

Reaction equation

HRID 456078 reaction equation
[CH2:1]([NH:8][C:9]([NH:11][NH2:12])=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[CH:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[CH2:24][C:25]1[N:29]2[N:30]=[C:31]([C:34](=O)[CH3:35])[CH:32]=[CH:33][C:28]2=[N:27][CH:26]=1>>[CH2:1]([NH:8][C:9]([NH:11]/[N:12]=[C:34](/[C:31]1[CH:32]=[CH:33][C:28]2[N:29]([C:25]([CH2:24][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][C:14]=3[F:13])[N:21]=[CH:20][CH:19]=[CH:18]4)=[CH:26][N:27]=2)[N:30]=1)\[CH3:35])=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7371353-Amino-1-benzylthioureaHCID 581905991-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]ethanone

Product 1

HCID 716998791-benzyl-3-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]thioureaYield 80%

Procedure

The title compound was prepared from N-benzylhydrazine carbothioamide and 1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-ethanone in analogy to the synthesis of example 1 in 80% yield. 1H-NMR (400 MHz, DMSO-d6) δ ppm 10.58 (s, 1H), 9.30 (t, 1H), 8.86 (dd, 1H), 8.30 (m, 2H), 8.05 (d, 1H), 7.95 (d, 1H), 7.77 (d, 1H), 7.69 (s, 1H), 7.47 (q, 1H), 7.32 (m, 4H), 7.23 (m, 1H), 4.89 (d, 2H), 4.58 (s, 2H), 2.39 (s, 3H). LCMS (method C): [MH]+=484, tR=4.18 min.

Sources & evidence

ORD record
ord-70e0ac505cc44e77ab5dc6d678e62eaa
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

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