Ethylmorpholine → 4-Chloro-7-[(1,1-dioxido-4-thiomorpholinyl)carbonyl]-1-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 733726노트

반응식

HRID 733726 반응식
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[C:5]([C:12]([OH:14])=O)=[CH:4][N:3]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.Cl.[NH:45]1[CH2:50][CH2:49][S:48](=[O:52])(=[O:51])[CH2:47][CH2:46]1>CN(C)C=O.O>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[C:5]([C:12]([N:45]2[CH2:50][CH2:49][S:48](=[O:52])(=[O:51])[CH2:47][CH2:46]2)=[O:14])=[CH:4][N:3]=1

참가 물질

8

반응물 5

HCID 7525EthylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 12324096Thiomorpholine 1,1-dioxide hydrochlorideHCID 578409034-Chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid

생성물 1

HCID 578409984-Chloro-7-[(1,1-dioxido-4-thiomorpholinyl)carbonyl]-1-methyl-1H-pyrrolo[3,2-c]pyridine수율 80.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid (726 mg) in dimethylformamide (12 ml) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (0.73 g), 1-hydroxybenzotriazole (0.52 g), N-ethylmorpholine (0.48 ml) and thiomorpholine 1,1-dioxide hydrochloride (0.66 g). The solution was stirred at room temperature overnight. The reaction was diluted with water and extracted three times with ethyl acetate. The ethyl acetate layers were combined, washed with saturated sodium chloride solution and dried (MgSO4) then evaporated. The residue was triturated with diethyl ether/n-hexane and filtered to afford the title compound as an off-white solid (0.907 g).

후처리

  1. extractionextracted three times with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. customthen evaporated
  5. customThe residue was triturated with diethyl ether/n-hexane
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-8569668736d3408f894c12450a0682af
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589206B2

반응 노트

불러오는 중…