Triethylamine → (4-Ethoxy-phenyl)-{4-[1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanone

HRID 1958390ノート

反応式

HRID 1958390 の反応式
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]2=[N:17][CH:18]=[N:19][C:20]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[C:15]2[CH:14]=[N:13]1.C(N(CC)CC)C.[CH2:35]([O:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)[CH3:36]>C1COCC1>[CH2:35]([O:37][C:38]1[CH:46]=[CH:45][C:41]([C:42]([N:25]2[CH2:24][CH2:23][CH:22]([O:21][C:20]3[N:19]=[CH:18][N:17]=[C:16]4[N:12]([C:3]5[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:9])=[O:10])=[CH:7][C:2]=5[F:1])[N:13]=[CH:14][C:15]=34)[CH2:27][CH2:26]2)=[O:43])=[CH:40][CH:39]=1)[CH3:36]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1400594-Ethoxybenzoyl ChlorideHCID 218975531-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

生成物 1

HCID 21897676(4-Ethoxy-phenyl)-{4-[1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

In a 50 mL round-bottomed flask fitted with N2 inlet was placed 1-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (50 mg, 0.117 mmol) and triethylamine (65 μl) and THF (0.8 mL). The reaction flask was immersed in an ice-bath. 4-Ethoxy-benzoyl chloride (24 mg, 0.129 mmol) was added to the solution and the mixture was stirred 2 h under N2 at 0° C. After all of the starting amine was completely converted as indicated by LCMS, the reaction was stopped by quenching with water. The reaction mixture was then concentrated under vacuum and purified by column chromatography using EtOAc as eluent to give Compound A184. 1H NMR (CDCl3, 400 MHz) δ 1.43 (t, 3H), 1.96 (m, 2H), 2.17 (m, 2H), 3.13 (s, 3H), 3.55 (m, 2H), 4.06 (m, 2H), 4.12 (m, 2H), 5.71 (m, 1H), 6.92 (d, 2H), 7.43 (d, 2H), 7.92 (m, 3H), 8.33 (s, 1H), 8.62 (s, 1H). Exact mass calculated for C26H26FN5O5S 539.16, found 540.2 (MH+).

後処理

  1. customIn a 50 mL round-bottomed flask fitted with N2 inlet
  2. customThe reaction flask was immersed in an ice-bath
  3. customby quenching with water
  4. concentrationThe reaction mixture was then concentrated under vacuum
  5. custompurified by column chromatography
  6. customto give Compound A184

出典と根拠

ORDレコード
ord-fc65af67f40c446eaa9c615d5ede480e
出典データセット
uspto-grants-2013_04
特許番号
US08410119B2

反応ノート

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