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Acetyl chloride → (R)-1-(3 acetyl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea

HRID 590845
ノート
印刷プレビュー

反応式

HRID 590845 の反応式
[C:1]1([C@H:7]([NH:9][C:10]([NH:12][C:13]2[CH:22]=[C:21]3[NH:23][N:24]=[C:19]4[C:20]3=[C:15]([CH2:16][CH2:17][NH:18]4)[N:14]=2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>C(Cl)Cl>[C:32]([N:18]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([NH:12][C:10]([NH:9][C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH3:8])=[O:11])[CH:22]=[C:21]3[NH:23][N:24]=[C:19]1[C:20]=23)(=[O:34])[CH3:33]
参加物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 6367Acetyl chlorideHCID 8471TriethylamineHCID 136236929(R)-1-(1-phenylethyl)-3-(1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)urea

生成物 1

HCID 73505230(R)-1-(3 acetyl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

(R)-1-(1-phenylethyl)-3-(1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)urea (Example 136; 13 mg, 0.040 mmol) and triethylamine (50 mg, 0.494 mmol) were taken in DCM (0.15 mL) and added acetyl chloride (20 mg, 0.255 mmol) and stirred for 1 hour. The reaction mixture was diluted with DCM, washed with aqueous sodium bicarbonate, brine, dried with sodium sulfate and concentrated. Purification of the residue by flash column (0-15% MeOH-DCM) gave (R)-1-(3 acetyl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridin-7-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C19H20N6O2 [M+H]+ 365. found 365. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 12.35 (s, 1H), 9.13-9.05 (m, 1H), 8.05-7.86 (m, 1H), 7.39-7.28 (m, 6H), 7.27-7.18 (m, 1H), 3.06-2.96 (m, 2H), 1.38 (t, J=9.1, 3H), 1.25-1.18 (m, 2H).

後処理

  1. washwashed with aqueous sodium bicarbonate, brine
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated
  4. customPurification of the residue by flash column (0-15% MeOH-DCM)

出典と根拠

ORDレコード
ord-301f18ea1086420e8632247470c8a6bb
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09233979B2

反応ノート

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