N-(6-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-ylthio)imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide → 3-(2-(Cyclopropanecarboxamido)imidazo[1,2-b]pyridazin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid

HRID 1925127Notes

Reaction equation

HRID 1925127 reaction equation
[SH:1][C:2]1[N:6]2[CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.BrC1C=CC2N(C(S[C:25]3[CH:26]=[CH:27][C:28]4[N:29]([CH:31]=[C:32]([NH:34][C:35]([CH:37]5[CH2:39][CH2:38]5)=[O:36])[N:33]=4)[N:30]=3)=NN=2)C=1>>[CH:37]1([C:35]([NH:34][C:32]2[N:33]=[C:28]3[CH:27]=[CH:26][C:25]([S:1][C:2]4[N:6]5[CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=[CH:10][C:5]5=[N:4][N:3]=4)=[N:30][N:29]3[CH:31]=2)=[O:36])[CH2:38][CH2:39]1

Participants

3

Reactant 2

HCID 46174984N-(6-(6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-ylthio)imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamideHCID 178524185HCID 178524185, compound

Product 1

HCID 592332813-(2-(Cyclopropanecarboxamido)imidazo[1,2-b]pyridazin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid

Procedure

Compound 33 was prepared from 3-mercapto-[1,2,4]triazolo[4,3-a]pyridine-6-carboxylic acid following the procedure described in the synthesis of compound 4. 1H NMR (400 MHz, CDCl3—CD3OD 10:1) δ ppm 9.03 (bs, 1 H), 8.01 (d, J=9.1 Hz, 1 H), 7.87 (d, J=9.6 Hz, 1 H), 7.68 (d, J=9.4 Hz, 1 H), 7.36 (m, 1H), 7.09 (d, J=9.3 Hz, 1 H), 2.84 (m, 1 H), 1.72 (m, 1 H), 0.97 (m, 2 H), 0.84 (m, 2H) ESI-MS:m/z 396.1 (M+H)+.

Sources & evidence

ORD record
ord-184972d282894218a6792394db7bf3b0
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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