Sodium hydride → (E)-2-(2-(6-Chloro-8-morpholino-3-(pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)vinyl)quinoline-5-carboxylic acid

HRID 718693Notes

Reaction equation

HRID 718693 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:16]P(OCC)(OCC)=O)=[N:11][C:12]=2[CH:13]=[CH:14][CH:15]=1)=[O:5])C.[H-].[Na+].[Cl:27][C:28]1[CH:29]=[C:30]([N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)[C:31]2[N:32]([C:34]([C:39]3[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=3)=[C:35]([CH:37]=O)[N:36]=2)[N:33]=1>CN(C=O)C>[Cl:27][C:28]1[CH:29]=[C:30]([N:45]2[CH2:50][CH2:49][O:48][CH2:47][CH2:46]2)[C:31]2[N:32]([C:34]([C:39]3[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=3)=[C:35](/[CH:37]=[CH:16]/[C:10]3[CH:9]=[CH:8][C:7]4[C:6]([C:4]([OH:3])=[O:5])=[CH:15][CH:14]=[CH:13][C:12]=4[N:11]=3)[N:36]=2)[N:33]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1177283226-Chloro-8-morpholino-3-(pyridin-3-yl)imidazo[1,2-b]pyridazine-2-carbaldehydeHCID 117732530Ethyl 2-[(diethoxyphosphinyl)methyl]-5-quinolinecarboxylate

Product 1

HCID 117728468(E)-2-(2-(6-Chloro-8-morpholino-3-(pyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)vinyl)quinoline-5-carboxylic acidYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of compound 73d (90 mg, 0.26 mmol) in DMF (3 mL) was added NaH (29 mg, 0.72 mmol) in one portion. Compound 73f (88 mg, 0.26 mmol) was then added as a slurry in DMF (1 mL). The reaction mixture was stirred for 10 min, quenched with water (1 mL) and acidified to pH 5 with 10% citric acid. The solid formed was collected by filtration, washed with water (2 mL), diethyl ether (5 mL), and dried under reduced pressure to afford compound 73g (107 mg). Mass spectrum (LCMS, ESI pos.) Calcd. For C27H21ClN6O3: 513.1 (M+H). found 512.8.

Workup

  1. customquenched with water (1 mL)
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with water (2 mL), diethyl ether (5 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1be5fc7427364ee89d739155c21bb4cd
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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