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

HRID 1364063ノート

反応式

HRID 1364063 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fc9d16d804a542fab3044ad163ee3195
出典データセット
uspto-grants-2011_02
特許番号
US07888349B2

反応ノート

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