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

Sodium Carbonate → cis-2,6-Dimethyl-4-{5-(2-methyl-4-pyridinyl)-4-[2-(trifluoromethyl)-3-pyridinyl]-2-pyrimidinyl}morpholine hydrochloride

HRID 2278454
노트
인쇄 미리보기

반응식

HRID 2278454 반응식
C(=O)([O-])[O-].[Na+].[Na+].[F:7][C:8]([F:19])([F:18])[C:9]1[C:14](B(O)O)=[CH:13][CH:12]=[CH:11][N:10]=1.[Cl:20][C:21]1[C:26]([C:27]2[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=2)=[CH:25][N:24]=[C:23]([N:34]2[CH2:39][C@H:38]([CH3:40])[O:37][C@H:36]([CH3:41])[CH2:35]2)[N:22]=1>O.COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[ClH:20].[CH3:40][C@H:38]1[O:37][C@@H:36]([CH3:41])[CH2:35][N:34]([C:23]2[N:24]=[C:25]([C:14]3[C:9]([C:8]([F:19])([F:18])[F:7])=[N:10][CH:11]=[CH:12][CH:13]=3)[C:26]([C:27]3[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=3)=[CH:21][N:22]=2)[CH2:39]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 44717660[2-(Trifluoromethyl)pyridin-3-yl]boronic acidHCID 86702425cis-4-(4-Chloro-5-(2-methylpyridin-4-yl)pyrimidin-2-yl)-2,6-dimethylmorpholine

생성물 1

HCID 86702433cis-2,6-Dimethyl-4-{5-(2-methyl-4-pyridinyl)-4-[2-(trifluoromethyl)-3-pyridinyl]-2-pyrimidinyl}morpholine hydrochloride수율 20.5%

시약·촉매·용매 3

HCID 6102075
Dichlorobis(triphenylphosphine)palladium
촉매
HCID 962Water용매
HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

Sodium carbonate (166 mg, 1.568 mmol) in water (2 ml), bis(triphenylphosphine) palladium(II)chloride (11.01 mg, 0.016 mmol) and [2-(trifluoromethyl)-3-pyridinyl]boronic acid (90 mg, 0.471 mmol) were added to a solution of cis-4-[4-chloro-5-(2-methyl-4-pyridinyl)-2-pyrimidinyl]-2,6-dimethylmorpholine (100 mg, 0.314 mmol) in 1,2-dimethoxyethane (DME) (3 ml). The reaction mixture was heated to 80° C. for 1 hour. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate (20 mls) and water (20 mls). The organic layer was passed through a hydrophobic frit to remove traces of water and then evaporated to dryness to give a yellow gum. The residue was subject to MDAP purification in 1 ml of 50:50 DMSO:MeOH. Clean fractions were combined and evaporated to dryness to give a yellow gum. The free base was generated by partitioning between sodium bicarbonate and dichloromethane. The organic layer was dried by passing through a hydrophobic frit and then the HCl salt was generated by addition of 1M HCl in diethylether (97 ul). The solvent was evaporated and the residue was co-evaporated with ether. The residue was triturated with ether and the resulting solid was collected and dried at 40° C. under vacuum for 1 hour to give the title compound as a yellow solid (30 mg, 19.5%). LC/MS [M+H]+=430. 1H NMR (400 MHz, d6-DMSO): δ 8.64 (1H, s), 8.60 (1H, d), 8.53 (1H, d), 8.32 (1H, t), 7.97 (1H, d), 7.67 (1H, m), 7.53-7.44 (1H, m), 4.70 (2H, d), 3.68-3.55 (2H, m), 2.75-2.65 (2H, m), 2.58 (3H, s), 1.19 (6H, d).

후처리

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between ethyl acetate (20 mls) and water (20 mls)
  3. customto remove traces of water
  4. customevaporated to dryness
  5. customto give a yellow gum
  6. customThe residue was subject to MDAP purification in 1 ml of 50:50 DMSO
  7. customevaporated to dryness
  8. customto give a yellow gum
  9. customby partitioning between sodium bicarbonate and dichloromethane
  10. customThe organic layer was dried
  11. additionthe HCl salt was generated by addition of 1M HCl in diethylether (97 ul)
  12. customThe solvent was evaporated
  13. customThe residue was triturated with ether
  14. customthe resulting solid was collected
  15. customdried at 40° C. under vacuum for 1 hour

출처 및 근거

ORD 기록
ord-93c1d61319714a8ca4d365ecfb7f6f16
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133178B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트