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

2-Methyl-3-butyn-2-ol → 8-Fluoro-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide

HRID 575090
노트
인쇄 미리보기

반응식

HRID 575090 반응식
Br[C:2]1[C:3]([F:19])=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[S:10][C:9]([C:15]([NH2:17])=[O:16])=[N:8][C:7]=3[C:6]=2[CH:18]=1.[CH3:20][C:21]([OH:25])([C:23]#[CH:24])[CH3:22]>CS(C)=O.C(N(CC)CC)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:19][C:3]1[C:2]([C:24]#[C:23][C:21]([OH:25])([CH3:22])[CH3:20])=[CH:18][C:6]2[C:7]3[N:8]=[C:9]([C:15]([NH2:17])=[O:16])[S:10][C:11]=3[CH2:12][CH2:13][O:14][C:5]=2[CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 2

HCID 82582-Methyl-3-butyn-2-olHCID 866930599-Bromo-8-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide

생성물 1

HCID 866931198-Fluoro-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 679Dimethyl Sulfoxide
용매
HCID 962Water용매
HCID 8471Triethylamine용매

실험 절차

The title compound was prepared according to a procedure similar to that described in Procedure G. Into a 8-mL sealed tube purged and maintained with an inert atmosphere of nitrogen, was placed a suspension of 9-Bromo-8-fluoro-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide (300 mg, 0.87 mmol, 1.00 equiv), 2-methylbut-3-yn-2-ol (260 mg, 3.09 mmol, 3.50 equiv) and Pd(PPh3)2Cl2 (60 mg, 0.09 mmol, 0.10 equiv) in DMSO (1 mL) and triethylamine (1 mL). The final reaction mixture was irradiated with microwave radiation for 1 h at 70° C. The resulting solution was diluted with 20 mL of water. The solids were collected by filtration and washed with 20 mL of ethyl acetate. This resulted in 0.24 g (79%) of 8-Fluoro-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide as a off-white solid. LC-MS (ES, m/z): 347[M+H]+; 1H-NMR: (300 MHz, DMSO-d6, ppm) δ 8.652 (d, 1H), 8.460 (s, 1H), 7.860 (s, 1H), 7.007 (d, 1H), 5.497 (s, 1H), 4.391 (t, 2H), 3.414 (t, 2H), 1.491 (s, 6H).

후처리

  1. customInto a 8-mL sealed tube
  2. custompurged
  3. temperaturemaintained with an inert atmosphere of nitrogen
  4. customThe final reaction mixture
  5. customwas irradiated with microwave radiation for 1 h at 70° C
  6. filtrationThe solids were collected by filtration
  7. washwashed with 20 mL of ethyl acetate
  8. customThis resulted in 0.24 g (79%) of 8-Fluoro-9-(3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide as a off-white solid

출처 및 근거

ORD 기록
ord-54ee7af7eabd4419b76da5c86b629a24
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09034866B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트