Water → 1-[5-(Cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-alpha]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one

HRID 724003Notes

Reaction equation

HRID 724003 reaction equation
[CH:1]1([NH:6][C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[C:14]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[C:15]([C:16](=[O:18])[CH3:17])=[C:9]3[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.CO[CH:30](OC)[N:31]([CH3:33])[CH3:32]>>[CH:1]1([NH:6][C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[C:14]([C:19]4[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=4)[C:15]([C:16](=[O:18])[CH:17]=[CH:30][N:31]([CH3:33])[CH3:32])=[C:9]3[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 962WaterHCID 78373Dimethylformamide dimethyl acetalHCID 114509291-[5-(Cyclopentylamino)-2-(4-methoxyphenyl) pyrazolo[1,5-alpha]pyridin-3-yl]ethanone

Product 1

HCID 693555081-[5-(Cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-alpha]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-oneYield 80%

Procedure

A solution of 1-[5-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3yl]ethanone (1.14 g, 3.26 mmol) in N,N-dimethylformamide dimethyl acetal (25 mL) was heated at reflux for 5 days. The mixture was allowed to cool to room temperature. Water was added and the resulting mixture was extracted with ethyl acetate. The organic phase was dried (magnesium sulfate), filtered and concentrated. The resulting residue was crystallized from ethyl acetate to give 1-[5-(cyclopentylamino)-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (1.05 g, 80%) as a yellow solid. 1H NMR (CDCl3): δ 8.11 (d, 1H), 7.56 (m, 3H), 7.41 (d, 1H), 6.95 (d, 2H), 6.22 (dd, 1H), 5.07 (d, 1H), 4.11 (d, 1H), 3.95 (m, 1H), 3.84 (s, 3H), 3.0–2.3 (broad, 6H), 2.12 (m, 2H), 1.74–1.48 (m, 6H); MS m/z 405 (M+1).

Workup

  1. temperatureat reflux for 5 days
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c912f6dc6b754130a20f214f2982e3df
Source dataset
uspto-grants-2006_11
Patent number
US07141569B2

Reaction notes

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