Hydrochloric Acid → 4-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-indazol-3-amine

HRID 1909925노트

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HRID 1909925 반응식
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[N:4]([CH3:27])[N:3]=1.Cl>CCO>[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[C:2]([NH2:1])=[N:3][N:4]4[CH3:27])=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 668240801,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate

생성물 1

HCID 668237234-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-indazol-3-amine수율 91.7%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
75 °C

실험 절차

To a stirred suspension of 1,1-dimethylethyl 5-(3-amino-1-methyl-1H-indazol-4-yl)-2,3-dihydro-1H-indole-1-carboxylate (1.70 g, 4.66 mmol) in 20 mL of EtOH was added 12 mL of 2N HCl. The mixture was heated at 75° C. for 90 min. LCMS showed conversion complete. The mixture was cooled, and concentrated in vacuo. The oily residue was diluted with 40 mL of water, and the pH was adjusted to ˜10 by adding 1N NaOH (pH paper). The milky mixture was extracted with 10° A MeOH in DCM (100 mL, then 2×25 mL). The combined organic was dried over Na2SO4, filtered, and concentrated in vacuo to give 4-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-indazol-3-amine as a brownish foamy solid (1.13 g). LC-MS (ES) m/z=265 [M+H]+.

후처리

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additionThe oily residue was diluted with 40 mL of water
  4. additionby adding 1N NaOH (pH paper)
  5. extractionThe milky mixture was extracted with 10° A MeOH in DCM (100 mL
  6. dry with materialThe combined organic was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-779ac28084634a5fb1ab05999f1487ae
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598156B2

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