홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-(5-Chloroindol-2-ylsulphonyl)-4-[6-(4-pyridyl)nicotinoyl]piperazine

HRID 2085914
노트
인쇄 미리보기

반응식

HRID 2085914 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=2)=[CH:3][CH:2]=1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([S:26]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)(=[O:28])=[O:27])=[CH:20]2.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[Cl:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([S:26]([N:29]1[CH2:34][CH2:33][N:32]([C:11](=[O:13])[C:10]3[CH:14]=[CH:15][C:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[N:8][CH:9]=3)[CH2:31][CH2:30]1)(=[O:28])=[O:27])=[CH:20]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22709453[2,4'-Bipyridine]-5-carboxylic acidHCID 227105715-chloro-2-(piperazine-1-sulfonyl)-1H-indole

생성물 1

HCID 98913881-(5-Chloroindol-2-ylsulphonyl)-4-[6-(4-pyridyl)nicotinoyl]piperazine수율 70.5%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

실험 절차

A stirred suspension of 6-(4-pyridyl)nicotinic acid (400 mg, 2 mmol) in dimethylformamide, DMF, (10 ml) was treated with 1-(5-chloroindol-2-ylsulphonyl)piperazine (600 mg, 2 mmol, 1 mol eq.) and 1-(3-dimethylaminopropyl)-3-ethylcarbodi-imide hydrochloride (EDAC, 460 mg, 2.4 mmol, 1.2 mol eq.). After stirring overnight the solvent was removed in vacuo and the residue chromatographed (Isolute 20 g silica cartridge, eluting with dichloromethane containing 2.5%-5% v/v of methanol) to yield 1-(5-chloroindol-2-ylsulphonyl)-4-[6-(4-pyridyl)nicotinoyl]piperazine as a colourless foam (680 mg). This was dissolved in dichloromethane/methanol mixture (40 ml of 1:1) and treated with a saturated solution of HCI in methanol until acid to indicator paper (slight excess). The resulting solution of hydrochloride salt was evaporated to dryness and the residue boiled in 2-propanol (100 ml, incomplete solution). Filtration and cooling gave 1-(5-chloroindol-2-ylsulphonyl)-4-[6-(4-pyridyl)nicotinoyl]piperazine hydrochloride as a colourless solid, (220 mg), 1H NMR (d6-DMSO) 3.0-3.3 (broad d, 4H), 3.6-4.0 (broad d, 4H), 7.05 (s, 1H), 7.35 (dd, 1H), 7.5 (d, 1H), 7.8 (d, 1H), 8.1 (dd, 1H), 8.35 (d, 1H), 8.5 (m, 2H), 8.8 (d, 1H), 8.95 (d, 2H), 12.4 (s, 1H), signals were also present due to 2-propanol (0.5 mol equiv.); MS (M+H)+ 481/483; mp 186-190° C. (not sharp).

후처리

  1. customwas removed in vacuo
  2. customthe residue chromatographed (Isolute 20 g silica cartridge
  3. washeluting with dichloromethane containing 2.5%-5% v/v of methanol)

출처 및 근거

ORD 기록
ord-9aa1dd140299491290fd1113bb771799
출처 데이터셋
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06723723B1

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트