Dimethylformamide dimethyl acetal → HCID 69423079, compound

HRID 1374724Notes

Reaction equation

HRID 1374724 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:18]([C:19](=[O:21])[CH3:20])=[C:11]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.CO[CH:24](OC)[N:25]([CH3:27])[CH3:26]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:18]([C:19](=[O:21])[CH:20]=[CH:24][N:25]([CH3:27])[CH3:26])=[C:11]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 17962425HCID 17962425, compound

Product 1

HCID 69423079HCID 69423079, compound

Conditions

Temperature
130 °C

Procedure

A mixture of 2-(4-fluorophenyl)-3-acetyl-6-cyanopyrazolo[1,5-a]pyridine (1.6 g, 5.6 mmol) and dimethylformamide-dimethylacetal (15 mL) was stirred and heated at 130° C., under N2, overnight. The solution was cooled and the resulting solid was collected by filtration and rinsed with acetone. The filtrate was evaporated and the resulting solid was purified using chromatography. The product solids were combined to afford the title compound as a brown solid, 1.3 g (68%). 1H NMR (d6-DMSO) showed a mixture of isomers. MS (ES+) m/z 335 (M++H), 264 (M+−70).

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe resulting solid was collected by filtration
  3. washrinsed with acetone
  4. customThe filtrate was evaporated
  5. customthe resulting solid was purified

Sources & evidence

ORD record
ord-a93811bd60574fa0bf99430bf8b8db29
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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