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Sodium ethoxide → Tert-butyl 4-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)piperazine-1-carboxylate

HRID 1921982
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반응식

HRID 1921982 반응식
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[C:9]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[CH:11]=2)=O.Cl.[CH3:34][N:35](N)[C:36]([NH2:38])=[NH:37].[O-]CC.[Na+]>C(O)C>[CH3:18][O:17][C:12]1[CH:11]=[C:10]2[C:15]([CH:16]=[C:7]([C:5]3[CH:4]=[CH:3][N:38]=[C:36]([NH:35][CH3:34])[N:37]=3)[CH:8]=[C:9]2[N:19]2[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:23][CH2:24]2)=[CH:14][CH:13]=1
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참가 물질

5

반응물 3

HCID 2723922Sodium ethoxide2회HCID 21432264Methyl amino guanidine hydrochlorideHCID 67306919(E)-tert-butyl 4-(3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate

생성물 1

HCID 53257824Tert-butyl 4-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 702
Ethanol
용매
2회

실험 절차

To a solution of tert-butyl 4-(3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)piperazine-1-carboxylate 108 (1.5 g) in ethanol (50 ml) was added methyl amino guanidine hydrochloride (0.75 g) and 21% wt sodium ethoxide in ethanol (1 ml). The reaction was stirred at reflux for 2 days, and more sodium ethoxide (0.5 ml) was added to the reaction. The reaction was allowed to reflux overnight. The solvents were concentrated under reduced pressure and the residue was redissolved in ethyl acetate (100 ml) and water (50 ml). The organics were separated, washed with water (1×50 ml), dried over sodium sulfate and concentrated. Column chromatography (pre-packed SiO2, 40% ethyl acetate in hexanes to 75% ethyl acetate in hexanes) gave tert-butyl 4-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)piperazine-1-carboxylate 111 as a light yellow solid. LC/MS (m/z): 450 [M+H].

후처리

  1. temperatureat reflux for 2 days
  2. temperatureto reflux overnight
  3. concentrationThe solvents were concentrated under reduced pressure
  4. dissolutionthe residue was redissolved in ethyl acetate (100 ml)
  5. customThe organics were separated
  6. washwashed with water (1×50 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1e401605b6584671998960ac8640d5e1
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173808B2

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