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

Methanol → N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-6-chlorobenzo[d]oxazol-2-amine

HRID 930292
노트
인쇄 미리보기

반응식

HRID 930292 반응식
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([F:36])=[C:14]([C@:16]4([CH3:35])[CH2:21][C@@H:20]([C:22]([F:25])([F:24])[F:23])[O:19][C:18]([NH:26]C(=O)C5C=CC=CC=5)=[N:17]4)[CH:15]=3)[O:8][C:4]=2[CH:3]=1.C1CCN2C(=NCCC2)CC1.CO>[NH4+].[Cl-].CCOC(C)=O>[NH2:26][C:18]1[O:19][C@H:20]([C:22]([F:25])([F:24])[F:23])[CH2:21][C@:16]([C:14]2[CH:15]=[C:10]([NH:9][C:7]3[O:8][C:4]4[CH:3]=[C:2]([Cl:1])[CH:38]=[CH:37][C:5]=4[N:6]=3)[CH:11]=[CH:12][C:13]=2[F:36])([CH3:35])[N:17]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 887MethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86732122N-((4S,6S)-4-(5-((6-chlorobenzo[d]oxazol-2-yl)amino)-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide

생성물 1

HCID 86732124N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-6-chlorobenzo[d]oxazol-2-amine수율 8%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매
HCID 25517Ammonium Chloride용매

반응 조건

온도
65 °C

실험 절차

A mixture of N-((4S,6S)-4-(5-((6-chlorobenzo[d]oxazol-2-yl)amino)-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (0.200 g, 0.366 mmol), DBU (0.072 mL, 0.475 mmol) and MeOH (3 mL) was stirred at 65° C. After 4 h, the mixture was diluted with saturated NH4Cl and EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The crude was purified by silica gel chromatography: 0-100% in 15 min, then 100% EtOAc-hexane. The product was obtained as a white solid (67.4 mg, 91% pure). The crude was further purified by reverse phase HPLC: 10-100% in 16 min, MeCN in water with 0.1% TFA. The combined fractions were neutralized with solid Na2CO3, and extracted with DCM three times. The organic phase was dried over Na2SO4 and concentrated in vacuo. The product was obtained as a white solid (12.7 mg, 8% yield). MS m/z=443 [M+H]+. Calculated for C19H15ClF4N4O2: 442.8.

후처리

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by silica gel chromatography
  5. wait0-100% in 15 min
  6. customThe product was obtained as a white solid (67.4 mg, 91% pure)
  7. customThe crude was further purified by reverse phase HPLC
  8. wait10-100% in 16 min
  9. extractionextracted with DCM three times
  10. dry with materialThe organic phase was dried over Na2SO4
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-03c016153e1e4681ae132702694758d6
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09296734B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트