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

1,2-Dichloroethane → diethyl ether (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)-2-(2-(6-morpholino-2,3-dioxoindolin-1-yl)acetoxy)ethyl)pyridine 1-oxide

HRID 571264
노트
인쇄 미리보기

반응식

HRID 571264 반응식
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[OH:10].C(Cl)CCl.[O:32]1[CH2:37][CH2:36][N:35]([C:38]2[CH:46]=[C:45]3[C:41]([C:42](=[O:52])[C:43](=[O:51])[N:44]3[CH2:47][C:48](O)=[O:49])=[CH:40][CH:39]=2)[CH2:34][CH2:33]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[O:10][C:48](=[O:49])[CH2:47][N:44]1[C:45]2[C:41](=[CH:40][CH:39]=[C:38]([N:35]3[CH2:34][CH2:33][O:32][CH2:37][CH2:36]3)[CH:46]=2)[C:42](=[O:52])[C:43]1=[O:51].[CH2:13]([O:21][CH2:22][CH3:23])[CH3:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 866816782-(6-Morpholino-2,3-dioxoindolin-1-yl)acetic acid

생성물 1

HCID 86681679diethyl ether (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)-2-(2-(6-morpholino-2,3-dioxoindolin-1-yl)acetoxy)ethyl)pyridine 1-oxide수율 44%

시약·촉매·용매

2
HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (0.200 g, 0.476 mmol) in DCM (15 ml), DMAP (0.070 g, 0.571 mmol), EDC (0.274 g, 1.428 mmol) and 2-(6-morpholino-2,3-dioxoindolin-1-yl)acetic acid (0.166 g, 0.571 mmol) were added in one portion at room temperature, and the resulting solution was stirred overnight. The solvent was removed under vacuum and the crude was purified by silica gel flash chromatography (DCM:MeOH=98:2) to afford a red solid. After trituration with diethyl ether (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)-2-(2-(6-morpholino-2,3-dioxoindolin-1-yl)acetoxy)ethyl)pyridine 1-oxide was obtained (0.145 mg, 0.209 mmol, 44% yield). MS/ESI+ 692.31 [MH]+; [αD]=+227.4, c=0.25, MeOH; 1H NMR (300 MHz, DMSO-d6) δ ppm 8.33 (s, 2H), 7.44 (d, 1H), 7.17 (d, 1H), 7.04 (d, 1H), 6.94 (dd, 1H), 7.08 (t, 1H), 6.59 (dd, 1H), 6.48 (d, 1H), 6.01 (dd, 1H), 4.56 (s, 2H), 3.90 (d, 2H), 3.63-3.80 (m, 4H), 3.43-3.55 (m, 4H), 3.37 (dd, 1H), 3.18 (dd, 1H), 1.13-1.35 (m, 1H), 0.50-0.66 (m, 2H), 0.23-0.48 (m, 2H)

후처리

  1. customThe solvent was removed under vacuum
  2. customthe crude was purified by silica gel flash chromatography (DCM:MeOH=98:2)
  3. customto afford a red solid

출처 및 근거

ORD 기록
ord-76db208b5f074759b7a71fe3fdeadbc0
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09024027B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트