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

HRID 2383421ノート

反応式

HRID 2383421 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ca93624297ca470da72c8a0530d4ea98
出典データセット
uspto-grants-2012_09
特許番号
US08263610B2

反応ノート

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