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

Ammonium Chloride → 6-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-cyclopropyl-phenyl)-amide

HRID 1094507
노트
인쇄 미리보기

반응식

HRID 1094507 반응식
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=2)[NH2:7])[CH2:3][CH2:2]1.C[Al](C)C.C[O:16][C:17]([C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:29][C:30]3[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][O:37][CH3:38])[N:31]=3)=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)=O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1.CCOC(C)=O.O>[CH:1]1([C:4]2[CH:5]=[C:6]([NH:7][C:17]([C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:29][C:30]5[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][O:37][CH3:38])[N:31]=5)=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)=[O:16])[CH:8]=[CH:9][CH:10]=2)[CH2:3][CH2:2]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 25517Ammonium ChlorideHCID 120321393-CyclopropylanilineHCID 16682925TrimethylaluminumHCID 591759856-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

생성물 1

HCID 236528666-(2-Methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (3-cyclopropyl-phenyl)-amide

시약·촉매·용매 4

HCID 962
Water
용매
HCID 1140Toluene용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
10 °C

실험 절차

In a dried vessel, 32.8 mg (0.247 mMol) 3-cyclopropyl-aniline [preparation see: Tet. Lett. 43 (2002) 6987] are dissolved in 4.3 ml toluene and cooled to 10° C. Then 370 μl Me3Al (2 M in toluene; 0.74 mMol) are added via syringe. After 1 h at rt, a solution of 80 mg (0.247 mMol) 6-(2-methoxymethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester (Step 15.4) in 1 ml THF is added and the reaction mixture is stirred for 30 min in an oil bath of 110° C. The solution is cooled in ice and hydrolyzed with 11 ml of a sat. NH4Cl. After 15 min stirring, the mixture is diluted with EtOAc and water, the aq. phase separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; toluene/acetone 99:1→4:1) gives the title compound: MS: [M+1]+=426; TLC (toluene/acetone 4:1): Rf=0.09.

후처리

  1. stirringAfter 15 min stirring
  2. customthe aq. phase separated off
  3. extractionextracted with EtOAc
  4. washThe organic layers are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ef89e87ade3f4b2b8f84421b0ac5f646
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08133886B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트