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Trifluoroacetic acid → HCID 73386767、化合物

HRID 1480767
ノート
印刷プレビュー

反応式

HRID 1480767 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:13][CH:12]([O:14][CH3:15])[CH2:11]2)=[O:9])=[CH:4][C:3]=1[O:16][CH3:17].C(O)(C(F)(F)F)=O.[CH3:25][N:26]1[CH:30]=[C:29]([C:31]2[C:36]3[N:37]=[C:38](S(C)(=O)=O)[N:39]=[CH:40][C:35]=3[CH:34]=[CH:33][N:32]=2)[CH:28]=[N:27]1>FC(F)(F)CO.CCOC(C)=O>[CH3:17][O:16][C:3]1[CH:4]=[C:5]([C:8]([N:10]2[CH2:13][CH:12]([O:14][CH3:15])[CH2:11]2)=[O:9])[CH:6]=[CH:7][C:2]=1[NH:1][C:38]1[N:39]=[CH:40][C:35]2[CH:34]=[CH:33][N:32]=[C:31]([C:29]3[CH:28]=[N:27][N:26]([CH3:25])[CH:30]=3)[C:36]=2[N:37]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 68310218HCID 68310218、化合物HCID 89996010HCID 89996010、化合物

生成物 1

HCID 73386767HCID 73386767、化合物収率 20.4%

試薬・触媒・溶媒 2

HCID 64092,2,2-Trifluoroethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (4-amino-3-methoxyphenyl)(3-methoxyazetidin-1-yl)methanone (Preparation 28, 56 mg, 0.237 mmol), TFA (46 μL, 0.601 mmol) and 8-(1-methyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrido[3,4-d]pyrimidine (Preparation 35, 35 mg, 0.121 mmol) in 2,2,2-trifluoroethanol (0.6 mL) was heated to reflux for 5 hours and then to 80° C. for 18 hours. The reaction was diluted with EtOAc, quenched with aqueous saturated NaHCO3 and the aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried, concentrated in vacuo and purified by silica gel column chromatography eluting with 0 to 100% EtOAc in cyclohexane followed by a second chromatography eluting with 0 to 10% MeOH in EtOAc to afford the title compound (11 mg, 20%). 1H 1HNMR (500 MHz, DMSO-d6): δ 9.43 (s, 1H), 9.17 (s, 1H), 8.64 (s, 1H), 8.40 (d, J=5.2 Hz, 1H), 8.28 (s, 1H), 8.05 (d, J=8.1 Hz, 1H), 7.62 (d, J=5.2 Hz, 1H), 7.42-7.28 (m, 2H), 4.56 (s, 1H), 4.33-4.20 (m, 3H), 3.89-3.87 (m, 7H), 3.25 (s, 3H).

後処理

  1. temperatureto reflux for 5 hours
  2. customquenched with aqueous saturated NaHCO3
  3. extractionthe aqueous layer extracted with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel column chromatography
  8. washeluting with 0 to 100% EtOAc in cyclohexane
  9. washeluting with 0 to 10% MeOH in EtOAc

出典と根拠

ORDレコード
ord-d74aff362a44465db511a47edd64f5f2
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409907B2

反応ノート

読み込み中…

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