Hydrochloric Acid → HCID 10184476, compound

HRID 861137Notes

Reaction equation

HRID 861137 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:28]4[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=4)[C:31]#N)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:36].[K+].Cl.C[OH:40]>>[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:28]4[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=4)[C:31]([OH:40])=[O:36])[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 10183232HCID 10183232, compound

Product 1

HCID 10184476HCID 10184476, compoundYield 19%

Conditions

Temperature
85 °C

Procedure

To a solution of 3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}benzonitrile (50 mg, 0.1 mmol) in methanol was added 4N potassium hydroxide. After heating at 85° C. for 2 days, the reaction mixture was cooled to room temperature and acidified with 2N hydrochloric acid. The solution was extracted with ethyl acetate. The organic phases were combined and dried over magnesium sulfate. Filtration and concentration, followed by purification by flash chromatography (90:10 ethyl acetate:methanol) gave 3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}benzoic acid (10 mg, 19%) as a brown foam. 1H NMR (CDCl3): δ 8.11 (s, 1H), 8.00 (d, 1H), 7.96 (d, 1H), 7.80 (broad s, 1H), 7.64 (d, 1H), 7.46 (t, 1H), 7.37 (t, 1H), 6.98 (d, 1H), 6.57 (d, 1H), 6.21 (d, 1H), 6.11 (broad, 1H), 4.12 (m, 1H), 4.01 (m, 1H), 2.06 (m, 2H), 1.88 (m, 2H), 1.69–1.49 (m, 12H). MS m/z 483 (M+1); 481 (M−1).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionThe solution was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration
  5. customfollowed by purification by flash chromatography (90:10 ethyl acetate:methanol)

Sources & evidence

ORD record
ord-b63af92b49c547e3979861b78ae8f226
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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