3-[2-(dimethylamino)ethoxy]benzaldehyde → HCID 178437846, compound

HRID 619168Notes

Reaction equation

HRID 619168 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][N:18]([CH3:30])[CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O>>[CH:1]1([N:6]2[C:10]3=[N:11][C:25]([C:24]4[CH:27]=[CH:28][CH:29]=[C:22]([O:21][CH2:20][CH2:19][N:18]([CH3:17])[CH3:30])[CH:23]=4)=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 108216053-[2-(dimethylamino)ethoxy]benzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437846HCID 178437846, compound

Conditions

Temperature
160 °C

Procedure

A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (3.50 g, 15.74 mmol), 3-[2-(dimethylamino)ethoxy]benzaldehyde (3.95 g) and xylenes (10 ml) was heated at 160° C. overnight. The reaction mixture was cooled to room temperature, the solvent was stripped, and the residue was partitioned between chloroform and water. The layers were separated, and the aqueous layer was extracted with chloroform. The organic layers were combined, washed with brine, dried over MgSO4, filtered and stripped to afford, as an oil, 1-cyclopentyl-3-ethyl-6-[3-[2-(dimethylamino)ethoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one labelled as [Example 23 (b)]. The free base was treated with ethanolic HCl to afford the product as the hydrochloride salt [labelled as Example 23 (c)].

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe residue was partitioned between chloroform and water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-49c77d89dd2542bcafb130749b2cda43
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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