Trimethylsilyl iodide → (S)-3-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)propyl isoquinolin-3-ylcarbamate

HRID 416429노트

반응식

HRID 416429 반응식
C(OC([NH:11][CH2:12][C@H:13]([N:29]([CH3:42])[C:30]([NH:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:35]=1[Cl:41])=[O:31])[CH2:14][O:15][C:16](=[O:28])[NH:17][C:18]1[N:19]=[CH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=O)C1C=CC=CC=1.[Si](I)(C)(C)C>CC#N>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[C:18]([NH:17][C:16](=[O:28])[O:15][CH2:14][C@@H:13]([N:29]([CH3:42])[C:30]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:35]=2[Cl:41])=[O:31])[CH2:12][NH2:11])[N:19]=1

참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 57947695Isoquinolin-3-yl-carbamic acid (S)-3-benzyloxycarbonylamino-2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-propyl ester

생성물 1

HCID 57947642(S)-3-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)propyl isoquinolin-3-ylcarbamate수율 275.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of isoquinolin-3-yl-carbamic acid (S)-3-benzyloxycarbonylamino-2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-propyl ester (1.3 g, 2.13 mmol) in CH3CN (20.0 mL) was added TMSI (0.35 mL, 2.56 mmol). The mixture was stirred at RT for 15 min and quenched with MeOH (20.0 mL). The resulting mixture was stirred for another 15 min, concentrated to dryness, and partitioned in between ether (30 mL) and HCl (2 N, 20 mL). The aqueous layer was separated, basified to pH 9, and extracted with EtOAc (200 mL×2). The combined organic layers were washed brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give (S)-3-amino-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)propyl isoquinolin-3-ylcarbamate (2.7 g) as a light yellow foam solid, which was used without further purification. LRMS (M+H+) m/z 460.1.

후처리

  1. customquenched with MeOH (20.0 mL)
  2. stirringThe resulting mixture was stirred for another 15 min
  3. concentrationconcentrated to dryness
  4. custompartitioned in between ether (30 mL) and HCl (2 N, 20 mL)
  5. customThe aqueous layer was separated
  6. extractionextracted with EtOAc (200 mL×2)
  7. washThe combined organic layers were washed brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0b471aa78782420badbcd6936684520d
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088793B2

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