Sodium Iodide → 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-3-(imidazo[1,2-a]pyrimidin-2-ylmethyl)dihydro-2H-pyran-2,4(3H)-dione

HRID 1453217

反応式

HRID 1453217 の反応式
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:16][CH2:17][C:18]2([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[O:23][C:22](=[O:24])[CH2:21][C:20](=[O:25])[CH2:19]2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].Cl[CH2:32][C:33]1[N:34]=[C:35]2[N:40]=[CH:39][CH:38]=[CH:37][N:36]2[CH:41]=1.[I-].[Na+]>CC(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:16][CH2:17][C:18]2([CH:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[O:23][C:22](=[O:24])[CH:21]([CH2:32][C:33]3[N:34]=[C:35]4[N:40]=[CH:39][CH:38]=[CH:37][N:36]4[CH:41]=3)[C:20](=[O:25])[CH2:19]2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14179082-(Chloromethyl)imidazo[1,2-a]pyrimidineHCID 160761096-(3-chloro-4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

生成物 1

HCID 575272716-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-3-(imidazo[1,2-a]pyrimidin-2-ylmethyl)dihydro-2H-pyran-2,4(3H)-dione収率 21.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Potassium carbonate (35.4 mg, 0.256 mmol) was added to a solution of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione (30 mg, 0.085 mmol), 2-(chloromethyl)imidazo[1,2-a]pyrimidine (17.2 mg, 0.103 mmol) and sodium iodide (5 crystals) in acetone (40 ml). The reaction mixture was stirred at reflux for 24 hrs, after which time the mixture was acidified to pH=3 and the product was extracted with ethyl acetate (3×25 ml). The combined organics were washed with brine (30 ml), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and purified by prep HPLC to afford the title compound as a white solid (8.8 mg). 1H NMR (CDCl3): δ 1.40-1.88 (bm, 11H), 2.24 (m, 2H), 2.48-2.59 (bm, 3H), 3.79 (s, 3H), 4.03 (d, J=14.08 Hz, 1H), 4.18 (d, J=14.08 Hz, 1H), 6.94 (d, J=1.60 Hz, 2H), 7.03 (d, J=1.60 Hz, 2H), 8.08 (s, 1H), 8.82 (bs, 1H), 8.85 (bs, 1H). Exact Mass: Calcd, 481.97; Found, 481.18.

後処理

  1. temperatureat reflux for 24 hrs
  2. extractionthe product was extracted with ethyl acetate (3×25 ml)
  3. washThe combined organics were washed with brine (30 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. custompurified by prep HPLC

出典と根拠

ORDレコード
ord-094bd833ebe64da3806a9ef62e3ede20
出典データセット
uspto-grants-2009_01
特許番号
US07473790B2

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