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Hydrochloric Acid → (1S,3R)-N1-(2-fluoro-5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)cyclohexane-1,3-diamine

HRID 74971
ノート
印刷プレビュー

反応式

HRID 74971 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[N:10](S(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=2)=[CH:4][C:3]=1[NH:28][C@H:29]1[CH2:34][CH2:33][CH2:32][C@@H:31]([NH:35]C(=O)OC(C)(C)C)[CH2:30]1.FC1C(N[C@H]2CCC[C@@H](NC(=O)OC(C)(C)C)C2)=NC(C2C3C(=NC=C(F)C=3)N(S(C3C=CC(C)=CC=3)(=O)=O)C=2)=NC=1.Cl>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[CH:4][C:3]=1[NH:28][C@H:29]1[CH2:34][CH2:33][CH2:32][C@@H:31]([NH2:35])[CH2:30]1
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 313Hydrochloric AcidHCID 68007251tert-butyl N-[(1R,3S)-3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]cyclohexyl]carbamateHCID 86667424HCID 86667424、化合物

生成物 1

HCID 68007687(1S,3R)-N1-(2-fluoro-5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)cyclohexane-1,3-diamine

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

反応条件

温度
50 °C

実験手順

To a solution of tert-butyl (1R,3S)-3-(2-fluoro-5-(5-fluoro-1-tosyl-1H-pyrrolo-[2,3-b]pyridin-3-yl)phenylamino)cyclohexylcarbamate, 44d, (0.65 g, 1.09 mmol) in methylene chloride (22 mL) was added hydrogen chloride (2.71 mL of 4M solution in 1,4-dioxane, 10.86 mmol). The reaction was heated to 50° C. and stirred for 6 hours. The mixture was cooled to room temperature and concentrated in vacuo, producing a yellow solid. The crude residue was purified via silica gel chromatography (25-50% Ethyl Acetate/hexanes gradient). Desired fractions were combined and concentrated in vacuo to produce 350 mg of 44e as a yellow powder.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customproducing a yellow solid
  4. customThe crude residue was purified via silica gel chromatography (25-50% Ethyl Acetate/hexanes gradient)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-550296620df449d88abda83892baf782
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08829007B2

反応ノート

読み込み中…

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