Hydrochloric Acid → HCID 178498897、化合物

HRID 1426971ノート

反応式

HRID 1426971 の反応式
[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

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 167693TrimethylsilyldiazomethaneHCID 66847769HCID 66847769、化合物

生成物 1

HCID 178498897HCID 178498897、化合物収率 93.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e19ab080dcbd4bf8a9a8018ce7986d4e
出典データセット
uspto-grants-2015_01
特許番号
US08933084B2

反応ノート

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