Triethylamine → 3,7-Dimethyl-3,7-diazabicyclo[3.3.1]non-9-yl-4-amino-5-chloro-2-(1-methyl-2-butynyl)oxybenzamide

HRID 343427

반응식

HRID 343427 반응식
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][C@@H:13]([CH3:17])[C:14]#[C:15][CH3:16])[CH:3]=1.ClC(OCC)=O.N[CH:25]1[CH:30]2[CH2:31][N:32]([CH3:34])[CH2:33][CH:26]1[CH2:27][N:28]([CH3:35])[CH2:29]2.[OH-].[Na+].C([N:40](CC)CC)C>ClCCl.O>[CH3:34][N:32]1[CH2:31][CH:30]2[CH:25]([C:3]3[C:4]([O:12][CH:13]([CH3:17])[C:14]#[C:15][CH3:16])=[C:5]([CH:9]=[C:10]([Cl:11])[C:2]=3[NH2:1])[C:6]([NH2:40])=[O:8])[CH:26]([CH2:27][N:28]([CH3:35])[CH2:29]2)[CH2:33]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 15258856(S)-4-amino-5-chloro-2-[(1-methyl-2-butynyl)oxy]benzoic acidHCID 543841879-Amino-3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane2회

생성물 1

HCID 867536153,7-Dimethyl-3,7-diazabicyclo[3.3.1]non-9-yl-4-amino-5-chloro-2-(1-methyl-2-butynyl)oxybenzamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 546 mg of (S)-4-amino-5-chloro-2-[(1-methyl-2-butynyl)oxy]benzoic acid and 0.9 ml of triethylamine in 10 ml of dichloromethane was cooled with ice, followed by the addition thereto of 0.225 ml of ethyl chloroformate. The obtained mixture was stirred for 10 minutes, while the temperature was brought to room temperature. 400 mg of 9-amino-3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane was added to the resulting mixture at room temperature. The obtained mixture was stirred for 30 minutes, followed by the addition thereto of 200 mg of 9-amino-3,7-dimethyl-3,7-diazabicyclo[3.3.1]nonane at room temperature. The obtained mixture was stirred for one hour, followed by the addition thereto of dichloromethane and water. The pH of the aqueous layer was adjusted to 10 or above with a 2.5N aqueous solution of sodium hydroxide. The organic phase was recovered, dried over anhydrous magnesium sulfate, and concentrated in a vacuum. The residue was purified by silica gel column chromatography (with 0 to 10 to 20% methanol/chloroform and then with chloroform/methanol/aqueous ammonia (75/25/1.5) to give 650 mg of the title compound.

후처리

  1. additionfollowed by the addition
  2. customwas brought to room temperature
  3. stirringThe obtained mixture was stirred for 30 minutes
  4. additionfollowed by the addition
  5. customat room temperature
  6. stirringThe obtained mixture was stirred for one hour
  7. additionfollowed by the addition
  8. customThe organic phase was recovered
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in a vacuum
  11. customThe residue was purified by silica gel column chromatography (with 0 to 10 to 20% methanol/chloroform

출처 및 근거

ORD 기록
ord-4ee68a094a724617842899cb012ae067
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05861418

연결된 노트

불러오는 중…