2-Methylindole → Methyl 1,2,3,4-tetrahydro-3-methyl-6-[(2-methyl-1H-indol-3-yl)methyl]-1-(isobutyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate

HRID 131557노트

반응식

HRID 131557 반응식
ClC1N=C(C)N([CH2:8][C:9]2[S:24][C:12]3[N:13]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:14](=[O:19])[N:15]([CH3:18])[C:16](=[O:17])[C:11]=3[C:10]=2C(N2C[C@H](O)CO2)=O)C=1Cl.BrN1C(=O)CC[C:36]1=O.[C:42](=[O:45])(O)[O-:43].[Na+].[CH3:47][C:48]1[NH:49][C:50]2[C:55]([CH:56]=1)=[CH:54][CH:53]=[CH:52][CH:51]=2>C(Cl)(Cl)Cl>[CH3:18][N:15]1[C:16](=[O:17])[C:11]2[C:10]([C:42]([O:43][CH3:36])=[O:45])=[C:9]([CH2:8][C:56]3[C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)[NH:49][C:48]=3[CH3:47])[S:24][C:12]=2[N:13]([CH2:20][CH:21]([CH3:22])[CH3:23])[C:14]1=[O:19]

참가 물질

6

반응물 4

HCID 72242-MethylindoleHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 101425596-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-5-[4-(S)-hydroxy-2-isoxazolidinylcarbonyl]-3-methyl-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 68805728Methyl 1,2,3,4-tetrahydro-3-methyl-6-[(2-methyl-1H-indol-3-yl)methyl]-1-(isobutyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of the product of example 3, part a), (7 g) and N-bromosuccinimide (4.42 g) in chloroform (140 ml) was refluxed under illumination from a tungsten lamp for 2 h. The solution was cooled to room temperature, saturated aqueous sodium bicarbonate solution (140 ml) and 2-methylindole (5.92 g) were added and the mixture stirred rapidly for 48 h. The phases were separated and the aqueous phase extracted with dichloromethane (100 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ethyl acetate/i-hexane (1:3) to give the sub-title compound as a pale brown solid (6.68 g). MS(ESI) 440 [M+H]+. δ 1HCDCl3 0.87 (6H, d), 2.11-2.21 (1H, m), 2.42 (3H, s), 3.38 (3H, s), 3.61 (2H, d), 3.99 (3H, s), 4.22 (2H, s), 7.08 (1H, t), 7.15 (1H, t), 7.31 (1H, d), 7.46 (1H, d), 7.91 (1H, s, br).

후처리

  1. customThe phases were separated
  2. extractionthe aqueous phase extracted with dichloromethane (100 ml)
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica
  7. washeluting with ethyl acetate/i-hexane (1:3)

출처 및 근거

ORD 기록
ord-a96c79dccaf74c48ae08fb7770008f4c
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384950B2

반응 노트

불러오는 중…