Dimethylamine → HCID 10023493, compound

HRID 902036Notes

Reaction equation

HRID 902036 reaction equation
C[Al](C)C.[CH3:5][NH:6][CH3:7].C([O:10][C:11]([C:13]1[CH:18]=[CH:17][N:16]2[N:19]=[C:20]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[C:21]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[CH:24][CH:23]=3)=[C:15]2[CH:14]=1)=O)C.C([O-])(=O)C(C(C([O-])=O)O)O.[Na+].[K+]>C(Cl)Cl>[CH3:5][N:6]([CH3:7])[C:11]([C:13]1[CH:18]=[CH:17][N:16]2[N:19]=[C:20]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[C:21]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[CH:24][CH:23]=3)=[C:15]2[CH:14]=1)=[O:10]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 9855836Potassium sodium tartarateHCID 16682925TrimethylaluminumHCID 69222999HCID 69222999, compound

Product 1

HCID 10023493HCID 10023493, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add trimethylaluminium (0.54 mL, 1.08 mmoL) dropwise to a solution of dimethylamine (0.45 mL, 0.90 mmoL) in methylene chloride (1 mL) at 0° C. Warm to room temperature and stir for 1 hour. Add 2-pyridin-2-yl-3-quinolin-4-yl-pyrazolo[1,5-a]pyridine-5-carboxylic acid ethyl ester (177 mg, 0.45 mmol) in methylene chloride (4 mL), and stir at room temperature for 1 hour and at 80° C. for 24 hours. Cool the reaction mixture to room temperature. Add aqueous solution of potassium sodium tartarate (20 mL) and stir the solution for 1 hour. Separate the organic layers and extract the aqueous solution with methylene chloride (2×20 mL). Dry the combined organic layers with sodium sulfate and concentrate. Purify by flash column chromatography (SiO2, 20-30% methanol/methylene chloride) to give the title compound 54 mg (31%) as a yellow solid.

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. customSeparate the organic layers
  3. extractionextract the aqueous solution with methylene chloride (2×20 mL)
  4. dry with materialDry the combined organic layers with sodium sulfate
  5. concentrationconcentrate
  6. customPurify by flash column chromatography (SiO2, 20-30% methanol/methylene chloride)

Sources & evidence

ORD record
ord-a78ad76147a5485eafb5b3e3c4b6b10e
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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