Isopropylamine → HCID 10308898, compound

HRID 1269049Notes

Reaction equation

HRID 1269049 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](SC)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][N:3]=1.ClC1C=C(C=CC=1)C(OO)=O.[CH:36]([NH2:39])([CH3:38])[CH3:37]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:39][CH:36]([CH3:38])[CH3:37])[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 70297m-Chloroperbenzoic acidHCID 18446588HCID 18446588, compound

Product 1

HCID 10308898HCID 10308898, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

2-(2-Fluoro-4-pyridinyl)-3-[2-(methylsulfanyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine (0.18 g, 0.53 mmol) was dissolved in dichloromethane (10 mL) and the resulting solution cooled to 0° C. in an ice bath. To this solution was added dropwise 3-chloroperoxybenzoic acid (230 mg, 57–86%) in dichloromethane. This reaction mixture was stirred at 0° C. for 10 minutes. Additional dichloromethane was added and the reaction mixture was extracted with saturated aqueous potassium carbonate. The organic phase was dried over magnesium sulfate, filtered and concentrated to give a foam. This foam was dissolved in isopropylamine and heated to 50° C. for 2 hours. The resulting mixture was concentrated to a solid that was purified by by silica gel chromatography (1:1 ethyl acetate:hexane) give 90 mg (48%) of the title compound as a solid. 1H NMR (CDCl3): δ 8.56 (d, 1H), 8.31 (m, 2H), 8.19 (d, 1H), 7.52 (m, 1H), 7.40 (t, 1H), 7.33 (broad s, 1H), 7.02 (t, 1H), 6.45 (d, 1H), 5.20 (m, 1H), 4.20 (m, 1H), 1.31 (d, 5H); 19F NMR (CDCl3): 8–67.68; MS m/z 349 (M+1).

Workup

  1. extractionthe reaction mixture was extracted with saturated aqueous potassium carbonate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a foam
  6. temperatureheated to 50° C. for 2 hours
  7. concentrationThe resulting mixture was concentrated to a solid
  8. customthat was purified by by silica gel chromatography (1:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-a283040034a446b3809c07b29f66c872
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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