6-Chloroimidazo[1,2-b]pyridazine-3-carbaldehyde → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(4,6-difluoro-1-methyl-1H-indazol-5-yl)methanol

HRID 456093Notes

Reaction equation

HRID 456093 reaction equation
FC1C=C(F)C=C2C=1C=NN2C.ClC1C=CC2N(C(C=O)=CN=2)N=1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([C:32]([C:35]([C:38]3[C:39]([F:49])=[C:40]4[C:44](=[CH:45][C:46]=3[F:47])[N:43]([CH3:48])[N:42]=[CH:41]4)([OH:37])C)=[CH:33][N:34]=2)[N:31]=1>>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]2[N:30]([C:32]([CH:35]([C:38]3[C:39]([F:49])=[C:40]4[C:44](=[CH:45][C:46]=3[F:47])[N:43]([CH3:48])[N:42]=[CH:41]4)[OH:37])=[CH:33][N:34]=2)[N:31]=1

Participants

4

Reactant 3

HCID 114467026-Chloroimidazo[1,2-b]pyridazine-3-carbaldehydeHCID 579174794,6-Difluoro-1-methyl-1H-indazoleHCID 581475291-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-1-(4,6-difluoro-1-methyl-1H-indazol-5-yl)-ethanol

Product 1

HCID 58190595(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(4,6-difluoro-1-methyl-1H-indazol-5-yl)methanolYield 41%

Procedure

The title compound as a yellow solid (60 mg, 0.172 mmol, 41%) was synthesized from intermediate 4,6-Difluoro-1-methyl-1H-indazole (70 mg, 0.416 mmol) and 6-chloroimidazo[1,2-b]pyridazine-3-carbaldehyde (76 mg, 0.416 mmol) using the same procedure as described in the synthesis of compound 31.1. 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.08 (s, 1H), 8.03 (d, 1H), 7.85 (s, 1H), 7.26 (q, 2H), 6.76 (s, 1H), 4.03 (s, 3H). LCMS (method B): [MH]+=349.9, tR=2.12 min.

Sources & evidence

ORD record
ord-85a7151f47e64ec38ca80a96227e8fc6
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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