Hydrochloric Acid → [1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid

HRID 1887190노트

반응식

HRID 1887190 반응식
C[O:2][C:3](=[O:29])[CH2:4][N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][N:14]=[CH:15][C:8]=2[N:7]([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[CH3:26])[N:19]([CH3:27])[CH:18]=2)[C:6]1=[O:28].[OH-].[Li+].Cl.O>O1CCOCC1>[CH3:27][N:19]1[C:20]2[C:25](=[C:24]([CH3:26])[CH:23]=[CH:22][CH:21]=2)[C:17]([CH2:16][N:7]2[C:8]3[CH:15]=[N:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[N:5]([CH2:4][C:3]([OH:29])=[O:2])[C:6]2=[O:28])=[CH:18]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67502958[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid methyl ester

생성물 1

HCID 46853638[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid수율 67%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 70 mg of [1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid methyl ester in 1,4-dioxane (2.0 mL) is added lithium hydroxide solution (11 mg of lithium hydroxide monohydrate in 0.5 mL of water) at room temperature. The solution is stirred at the same temperature for 5 h. Then 1.0 mL of 1.0 M hydrochloric acid is added along with 50 mL of water. The mixture is extracted with ethyl acetate (3×50 mL) and the organic layers are combined, dried over magnesium sulfate and concentrated to give crude product. The crude product is rinsed with methanol (3.0 mL) and dichloromethane (5.0 mL) and the remaining light yellow solid is dried to give 45 mg (67%) of [1-(1,4-dimethyl-1H-indol-3-ylmethyl)-2,4-dioxo-1,4-dihydro-2H-pyrido[3,4-d]pyrimidin-3-yl]-acetic acid; LCMS (ESMS): m/z 379.16 (M+H+).

후처리

  1. extractionThe mixture is extracted with ethyl acetate (3×50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give crude product
  5. washThe crude product is rinsed with methanol (3.0 mL) and dichloromethane (5.0 mL)
  6. customthe remaining light yellow solid is dried

출처 및 근거

ORD 기록
ord-3e31de601a954818b8115c48278db403
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501749B2

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