Water → 2-methyl-5,8-dihydro-4H-pyrazolo[3,4-c]thiazolo[5,4-f]isoquinoline

HRID 2383421노트

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HRID 2383421 반응식
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]4[CH2:16][CH2:17][C:18]5[N:23]=[C:22]([CH3:24])[S:21][C:19]=5[C:20]=4[C:11]=3[CH:10]=[N:9]2)=CC=1.O.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[CH3:24][C:22]1[S:21][C:19]2[C:20]3[C:11]4[CH:10]=[N:9][NH:8][C:12]=4[N:13]=[CH:14][C:15]=3[CH2:16][CH2:17][C:18]=2[N:23]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 594908578-(4-methoxybenzyl)-2-methyl-5,8-dihydro-4H-pyrazolo[3,4-c]thiazolo[5,4-f]isoquinoline

생성물 1

HCID 594906302-methyl-5,8-dihydro-4H-pyrazolo[3,4-c]thiazolo[5,4-f]isoquinoline수율 19%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of 8-(4-methoxybenzyl)-2-methyl-5,8-dihydro-4H-pyrazolo[3,4-c]thiazolo[5,4-f]isoquinoline (0.6 g, 1.65 mmol) in trifluoroacetic acid (4 mL) was heated at 100° C. for 2 hours. The reaction mixture was poured into water (50 mL) and basified with aqueous potassium carbonate to pH of 11. The reaction mixture was then extracted with dichloromethane (3×75 mL). The combined organic extract was dried using sodium sulfate and concentrated under reduced pressure to give dark residue. The crude product was purified by flash column chromatography (SiO2, gradient from 100% chloroform to 2% methanol in chloroform) to give a residue, which was further purified by crystallization from methanol and isopropanol to give the desired product (0.076 g, 13%) as a solid. 1H NMR (DMSO-d6, 400 MHz): δ 13.49 (s, 1H), 8.04 (s, 1H), 8.02 (s, 1H), 3.16 (t, J=7.6 Hz, 2H), 3.0 (t, J=7.6 Hz, 2H), 2.70 (s, 3H); LCMS [M+H]: 243.

후처리

  1. extractionThe reaction mixture was then extracted with dichloromethane (3×75 mL)
  2. extractionThe combined organic extract
  3. customwas dried
  4. concentrationconcentrated under reduced pressure
  5. customto give dark residue
  6. customThe crude product was purified by flash column chromatography (SiO2, gradient from 100% chloroform to 2% methanol in chloroform)
  7. customto give a residue, which
  8. customwas further purified by crystallization from methanol and isopropanol

출처 및 근거

ORD 기록
ord-ca93624297ca470da72c8a0530d4ea98
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263610B2

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