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Ethanol → 6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(isothiazol-5-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 2173068
ノート
印刷プレビュー

反応式

HRID 2173068 の反応式
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[S:26][N:25]=[CH:24][CH:23]=2)[C:19]2[C:27](=[O:37])[N:28](C(OC(C)(C)C)=O)[CH2:29][C:18]=2[C:17]=1[F:38])=O)(C)(C)C.Cl.O1CCOCC1.CCO>CO>[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[S:26][N:25]=[CH:24][CH:23]=2)[C:19]2[C:27](=[O:37])[NH:28][CH2:29][C:18]=2[C:17]=1[F:38]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 702EthanolHCID 204431481,4-Dioxane hydrochlorideHCID 71164908tert-butyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-7-fluoro-4-(isothiazol-5-yl)-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

生成物 1

HCID 711649406-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(isothiazol-5-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one収率 44.6%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of tert-butyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-7-fluoro-4-(isothiazol-5-yl)-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (65.9 mg, 0.120 mmol) in MeOH (1.0 mL) was added 4N HCl/dioxane (1.0 mL, 4.00 mmol). The reaction mixture was heated to 60° C. for 1 hour and was subsequently concentrated in vacuo. The residue was triturated with EtOAc and filtered. The filter cake was washed with EtOAc to give a yellow solid, which was suspended into EtOH. The mixture was stirred at 80° C. for 30 minutes and allowed to cool to room temperature. The resulting precipitate was collected by filtration and washed with EtOH to yield a hydrochloride salt of the title compound as an off-white solid (18.6 mg, 40%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.36-1.55 (m, 2H), 1.58-2.06 (m, 6H), 3.77 (br s, 1H), 4.17-4.33 (m, 1H), 4.39-4.54 (m, 2H), 7.19 (d, J=5.86 Hz, 1H), 7.88 (br s, 3H), 8.62 (d, J=1.95 Hz, 1H), 8.69 (s, 1H), 8.97 (d, J=1.95 Hz, 1H). ESI-MS m/z [M+H]+ calc'd for C16H18FN5OS, 348. found, 348.

後処理

  1. concentrationwas subsequently concentrated in vacuo
  2. customThe residue was triturated with EtOAc
  3. filtrationfiltered
  4. washThe filter cake was washed with EtOAc
  5. customto give a yellow solid, which
  6. temperatureto cool to room temperature
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with EtOH

出典と根拠

ORDレコード
ord-bb3999ec80694793a2f0dd62fcd3ae05
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056873B2

反応ノート

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