Trifluoroacetic acid → HCID 178508699、化合物

HRID 521591ノート

反応式

HRID 521591 の反応式
I[C:2]1[C:3]([S:11][C:12]2[NH:13][C:14]3[C:19]([N:20]=2)=[C:18]([NH2:21])[N:17]=[CH:16][N:15]=3)=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.C(O)(C(F)(F)F)=O.C1C(=O)N(I)C(=O)C1>C(#N)C>[O:9]1[C:5]2[CH:4]=[C:3]([S:11][C:12]3[NH:13][C:14]4[C:19]([N:20]=3)=[C:18]([NH2:21])[N:17]=[CH:16][N:15]=4)[CH:2]=[CH:10][C:6]=2[CH2:7][CH2:8]1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 178508696HCID 178508696、化合物

生成物 1

HCID 178508699HCID 178508699、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

8-(5-iodo-2,3-dihydrobenzofuran-6-ylthio)-9H-purin-6-amine (S6-4) To a solution of S6-3 (40 mg, 0.14 mmol) in 6 mL of acetonitrile was added TFA (40 μL) and NIS (63 mg, 0.28 mmol). The resulting mixture was stirred at rt for 2 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (CH2Cl2:MeOH, 100:0 to 90:10) to afford S6-4 (48 mg, 53%) as a yellow gum. 1H NMR (500 MHz, CDCl3) δ 8.26 (s, 1H), 7.79 (s, 1H), 7.12 (s, 1H), 4.65 (t, J=8.8 Hz, 2H), 3.28 (t, J=8.7 Hz, 2H); MS (ESI) m/z 412.0 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (CH2Cl2:MeOH, 100:0 to 90:10)
  3. customto afford S6-4 (48 mg, 53%) as a yellow gum

出典と根拠

ORDレコード
ord-633ab5501562489f8c70743ce98681d2
出典データセット
uspto-grants-2016_05
特許番号
US09328114B2

反応ノート

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