Chloride → tert-butyl 6-amino-3-benzyloxy-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

HRID 1364063노트

반응식

HRID 1364063 반응식
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:12]([O:19][C:20]1[CH:29]=[C:28]2[C:23]([C:24]3[N:32]4[CH2:33][CH2:34][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:36][C:31]4=[N:30][C:25]=3[CH:26]=[N:27]2)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[NH4+:45].[Cl-]>C(Cl)(Cl)Cl>[NH2:45][C:26]1[C:25]2[N:30]=[C:31]3[CH2:36][N:35]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:34][CH2:33][N:32]3[C:24]=2[C:23]2[C:28](=[CH:29][C:20]([O:19][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:21][CH:22]=2)[N:27]=1

참가 물질

6

반응물 4

HCID 312ChlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 66958454tert-butyl 3-benzyloxy-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

생성물 1

HCID 66958130tert-butyl 6-amino-3-benzyloxy-10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

mCPBA (0.782 g of 77% purity, 3.49 mmol) was added to a solution of tert-butyl 3-benzyloxy-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate (1.0 g, 2.3 mmol) in chloroform (15 mL), and the reaction was stirred for 30 minutes. Ammonium hydroxide (5 mL), and the reaction was stirred for five minutes before the rapid addition of p-toluenesulfnyl chloride (0.4865 g, 2.55 mmol). The reaction was stirred overnight at ambient temperature. The organic layer was separated and concentrated under reduced pressure. The residue was purified by normal phase prep HPLC on silica gel (eluting with 2 N ammonia in methanol/chloroform in a 42-minute gradient from 0:100 to 5:95) to provide 550 mg of tert-butyl 6-amino-3-benzyloxy-10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate.

후처리

  1. stirringThe reaction was stirred overnight at ambient temperature
  2. customThe organic layer was separated
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by normal phase prep HPLC on silica gel (
  5. washeluting with 2 N ammonia in methanol/chloroform in a 42-minute gradient from 0:100 to 5:95)

출처 및 근거

ORD 기록
ord-fc9d16d804a542fab3044ad163ee3195
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888349B2

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