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

HRID 1864118

반응식

HRID 1864118 반응식
[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]

참가 물질

5

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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, 400MHz) 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+).

후처리

  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

출처 및 근거

ORD 기록
ord-2bbee932536546be938dbe36170d5d4c
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625906B2

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