Sodium Iodide → 2,2-dimethylmalonic acid 5-{(R)-(4-{amino(2,2-dimethylpropoxycarbonylimino)methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]-triazol-3-yloxymethyl ester isopropyl ester

HRID 2089658

반응식

HRID 2089658 반응식
[CH3:1][C:2]([CH3:46])([CH3:45])[CH2:3][O:4][C:5](=[O:44])[N:6]=[C:7]([NH2:43])[C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:15]([C:29]2[N:33]=[C:32]([O:34][CH2:35]Cl)[N:31]([C:37]3[N:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[N:30]=2)[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][CH2:26][OH:27])[C:17]=2[F:28])=[CH:10][CH:9]=1.C(=O)([O-])O.[K+].[I-].[Na+].[CH:54]([O:57][C:58](=[O:65])[C:59]([CH3:64])([CH3:63])[C:60]([OH:62])=[O:61])([CH3:56])[CH3:55]>CN(C=O)C>[CH:54]([O:57][C:58](=[O:65])[C:59]([CH3:63])([CH3:64])[C:60]([O:62][CH2:35][O:34][C:32]1[N:31]([C:37]2[N:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[N:30]=[C:29]([C@H:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH2:43])=[N:6][C:5]([O:4][CH2:3][C:2]([CH3:46])([CH3:45])[CH3:1])=[O:44])=[CH:9][CH:10]=2)[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH2:25][CH2:26][OH:27])[C:17]=2[F:28])[N:33]=1)=[O:61])([CH3:56])[CH3:55]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 516893Potassium BicarbonateHCID 212436462,2-Dimethylmalonic acid monoisopropyl esterHCID 67470504[1-amino-1-[4-({(5-chloromethoxy-1-pyrimidin-2-yl-1H-[1,2,4]triazol-3-yl)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)phenyl]methylidene]carbamic acid 2,2-dimethylpropyl ester

생성물 1

HCID 674704872,2-dimethylmalonic acid 5-{(R)-(4-{amino(2,2-dimethylpropoxycarbonylimino)methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]-triazol-3-yloxymethyl ester isopropyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
45 °C

실험 절차

To a mixture of [1-amino-1-[4-({(5-chloromethoxy-1-pyrimidin-2-yl-1H-[1,2,4]triazol-3-yl)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)phenyl]methylidene]carbamic acid 2,2-dimethylpropyl ester (Example 2b, 70 mg), potassium hydrogen carbonate (74 mg), and DMF (5 mL), sodium iodide (79 mg) and 2,2-dimethylmalonic acid monoisopropyl ester [CAS No. 7695-26-3] (92 mg) were added, and the resulting mixture was stirred at 45° C. overnight. The reaction mixture was filtered, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate) to obtain a racemate of the captioned compound.

후처리

  1. addition7695-26-3] (92 mg) were added
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate obtained
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate)
  7. customto obtain a racemate of the captioned compound

출처 및 근거

ORD 기록
ord-9496fde7d44b4d00b08cf654cc0bf02b
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436009B2

연결된 노트

불러오는 중…