Hydrochloric Acid → HCID 178498897, 화합물

HRID 1426971노트

반응식

HRID 1426971 반응식
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[C:17]3[N:16]=2)[C:5]([O:8]C)=[N:6][CH:7]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:28].Cl>CO.O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]([O:26][CH3:28])=[O:25])=[C:17]3[N:16]=2)[C:5]([OH:8])=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 167693TrimethylsilyldiazomethaneHCID 66847769HCID 66847769, 화합물

생성물 1

HCID 178498897HCID 178498897, 화합물수율 93.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

To a suspension of (R)-5-(2-(5-fluoro-2-methoxypyridin-3-yl) pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation B; 5.01 g, 14.0 mmol) in MeOH (150 mL) was added dropwise TMSCHN2 (8.41 mL, 16.8 mmol). The reaction was stirred for 30 minutes, and then quenched with 1 mL of acetic acid. The solvent was removed under reduced pressure and the residue was dried under high vacuum to give the crude methyl ester. To the crude methyl ester was added 4N HCl in dioxane (100 mL) and the reaction was sealed and heated to 90° C. for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in DCM (100 mL) and washed with saturated NaHCO3 (40 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude desired product (4.67 g, 93.2% yield). MS (apci) m/z=357.9 (M+H).

후처리

  1. customquenched with 1 mL of acetic acid
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was dried under high vacuum
  4. customto give the crude methyl ester
  5. customthe reaction was sealed
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in DCM (100 mL)
  8. washwashed with saturated NaHCO3 (40 mL)
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e19ab080dcbd4bf8a9a8018ce7986d4e
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933084B2

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