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

Morpholine → 1-(5-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-7-(4-morpholinyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]-thiazine 4,4-dioxide

HRID 1618677
노트
인쇄 미리보기

반응식

HRID 1618677 반응식
Cl[C:2]1[CH:31]=[N:30][C:5]2[S:6](=[O:29])(=[O:28])[CH2:7][CH2:8][N:9]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][C:18]=4[F:20])[N:13]=[C:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:11]=3[CH3:27])[C:4]=2[CH:3]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[NH:66]1[CH2:71][CH2:70][O:69][CH2:68][CH2:67]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:20][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[C:10]([N:9]1[CH2:8][CH2:7][S:6](=[O:29])(=[O:28])[C:5]3[N:30]=[CH:31][C:2]([N:66]4[CH2:71][CH2:70][O:69][CH2:68][CH2:67]4)=[CH:3][C:4]1=3)=[C:11]([CH3:27])[C:12]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)=[N:13]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8083MorpholineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23676156Sodium t-butoxideHCID 672857777-chloro-1-(5-fluoro-3-methyl-2-pyridin-2-ylquinolin-4-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine 4,4-dioxide

생성물 1

HCID 509393421-(5-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-7-(4-morpholinyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]-thiazine 4,4-dioxide

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

Prepared according to procedure N by heating a solution of 7-chloro-1-(5-fluoro-3-methyl-2-pyridin-2-ylquinolin-4-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine 4,4-dioxide (34 mg, 0.075 mmol), Pd2dba3 (6.8 mg, 7.5 μmol), XPhos (7.13 mg, 0.015 mmol), morpholine (6.51 μL, 0.075 mmol) and sodium tert-butoxide (14.4 mg, 0.149 mmol) in toluene (2.0 mL) in the microwave for 2 h at 110° C. After this time the reaction was cooled to rt and partitioned between EtOAc (60 mL) and NaHCO3 (20 mL, saturated aqueous solution). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Purification by reverse phase HPLC (10 to 60% acetonitrile in water) gave 1-(5-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-7-(4-morpholinyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]-thiazine 4,4-dioxide. 1H NMR (400 MHz, chloroform-d) δ ppm 8.75 (1H, dt, J=4.8, 1.5 Hz), 8.05-8.12 (1H, m), 7.94 (2H, dt, J=4.6, 0.9 Hz), 7.87 (1H, d, J=2.3 Hz), 7.70 (1H, td, J=8.2, 5.4 Hz), 7.44 (1H, q, J=4.8 Hz), 7.23-7.30 (1H, m), 5.62 (1H, d, J=2.3 Hz), 4.17-4.32 (2H, m), 3.64-3.76 (5H, m), 3.49-3.60 (1H, m), 2.87-3.04 (4H, m), 2.46 (3H, s). Mass Spectrum (ESI) m/e=506.0 (M+1).

후처리

  1. customPrepared
  2. custompartitioned between EtOAc (60 mL) and NaHCO3 (20 mL, saturated aqueous solution)
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by reverse phase HPLC (10 to 60% acetonitrile in water)

출처 및 근거

ORD 기록
ord-2cf46056a32049f0b93988914bf8addc
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765940B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트