Chloroform → HCID 66958260, compound

HRID 1364041Notes

Reaction equation

HRID 1364041 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[Si:12]([O:19][CH:20]1[CH2:37][N:25]2[C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:29]=[CH:28][C:27]=3[N:36]=[C:24]2[CH2:23][N:22]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:21]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(Cl)(Cl)Cl.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:61]>>[NH2:61][C:28]1[C:27]2[N:36]=[C:24]3[CH2:23][N:22]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:21][CH:20]([O:19][Si:12]([C:15]([CH3:16])([CH3:17])[CH3:18])([CH3:13])[CH3:14])[CH2:37][N:25]3[C:26]=2[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=1

Participants

6

Reactant 5

HCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 66958543HCID 66958543, compound

Product 1

HCID 66958260HCID 66958260, compound

Procedure

mCPBA (3.89 g of 77% pure material, 17.36 mmol) was added to a solution of tert-butyl 11-{[tert-butyl(dimethyl)silyl]oxy}-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate (4.07 g, 8.68 mol chloroform, and the reaction was stirred for 30 minutes at ambient temperature. Additional mCPBA (0.5 equivalent) was added, and the reaction was stirred for four hours. Ammonium hydroxide (50 mL) was added with vigorous stirring, and after ten minutes, p-toluenesulfonyl chloride (1.82 g, 9.55 mmol) was added. The reaction was stirred overnight at ambient temperature and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting sequentially with 98.5:1:0.5 and 89:10:1 dichloromethane:methanol:ammonium hydroxide), and the resulting product was dried under high vacuum to provide 2.25 g of tert-butyl 6-amino-11-{[tert-butyl(dimethyl)silyl]oxy}-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate.

Workup

  1. stirringthe reaction was stirred for four hours
  2. waitafter ten minutes
  3. stirringThe reaction was stirred overnight at ambient temperature
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (
  6. washeluting sequentially with 98.5:1:0.5 and 89:10:1 dichloromethane
  7. dry with materialmethanol:ammonium hydroxide), and the resulting product was dried under high vacuum

Sources & evidence

ORD record
ord-5a4b5b39a9e9412fa1b32ccac9d0db37
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

Loading…