HCID 71451823, compound → HCID 86682738, compound

HRID 1755391Notes

Reaction equation

HRID 1755391 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[N:12]=[C:11]([NH:13][C:14]2[C:15]3[N:16]([CH:28]=[CH:29][N:30]=3)[N:17]=[C:18]([C:20]3[CH:21]=[C:22]([CH2:26][OH:27])[CH:23]=[CH:24][CH:25]=3)[CH:19]=2)[CH:10]=[CH:9][CH:8]=1>ClCCl.O=[Mn]=O>[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[N:12]=[C:11]([NH:13][C:14]2[C:15]3[N:16]([CH:28]=[CH:29][N:30]=3)[N:17]=[C:18]([C:20]3[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=3)[CH:26]=[O:27])[CH:19]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 71451823HCID 71451823, compound

Product 1

HCID 86682738HCID 86682738, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

(3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)phenyl)methanol (20 mg, 0.05 mmol) and MnO2 (86 mg, 1.0 mmol) were dissolved in dichloromethane (10 mL), the reaction mixture was heated up to 40° C. with stirring for 24 h, filtered, washed with dichloromethane (30 mL) and then the filtrate was concentrated in vacuo to give a solid which was purified by chromatography on a aluminum oxide eluted with dichloromethane to give 3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzaldehyde (9 mg, 45%) as an orange solid. LC-MS: 399 [M+H]+, tR=1.88 min.

Workup

  1. filtrationfiltered
  2. washwashed with dichloromethane (30 mL)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give a solid which
  5. customwas purified by chromatography on a aluminum oxide
  6. washeluted with dichloromethane

Sources & evidence

ORD record
ord-c2c391ab321545739863899fe3aa2dde
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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