2-Naphthoic acid → Methyl {4-methyl-2-[4-(2-naphthoylamino)benzyl]-6-pyrrolidin-1-ylpyrimidin-5-yl}acetate

HRID 1159677

반응식

HRID 1159677 반응식
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[N:12]=[C:11]([CH3:13])[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:9]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:8]=2)=[CH:4][CH:3]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:59]1[C:68]2[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH:62]=[CH:61][C:60]=1[C:69](O)=[O:70].C(N(CC)C(C)C)(C)C>C1COCC1.O>[CH3:13][C:11]1[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:9]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[N:8]=[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:69]([C:60]3[CH:61]=[CH:62][C:63]4[C:68](=[CH:67][CH:66]=[CH:65][CH:64]=4)[CH:59]=3)=[O:70])=[CH:25][CH:24]=2)[N:12]=1

참가 물질

7

반응물 4

HCID 71232-Naphthoic acidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59514524Methyl[2-(4-aminobenzyl)-4-methyl-6-pyrrolidin-1-ylpyrimidin-5-yl]acetate

생성물 1

HCID 59514539Methyl {4-methyl-2-[4-(2-naphthoylamino)benzyl]-6-pyrrolidin-1-ylpyrimidin-5-yl}acetate수율 36.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl [2-(4-aminobenzyl)-4-methyl-6-pyrrolidin-1-ylpyrimidin-5-yl]acetate (0.034 g, 0.10 mmol) in THF (1 mL) at room temperature was treated with PyBOP (0.052 g, 0.10 mmol), 2-naphthoic acid (0.019 g, 0.11 mmol), and N,N-diisopropylethylamine (0.017 mL, 0.10 mmol). After stirring at room temperature for 17 hours, the reaction mixture was poured into water and extracted with EtOAc. The combined organic extracts was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The remaining residue was chromatographed over silica gel eluting with 60% EtOAc in CH2Cl2 to give methyl {4-methyl-2-[4-(2-naphthoylamino)benzyl]-6-pyrrolidin-1-ylpyrimidin-5-yl}acetate (0.018 g, 36% yield) as a yellow oil.

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe remaining residue was chromatographed over silica gel eluting with 60% EtOAc in CH2Cl2

출처 및 근거

ORD 기록
ord-b6b6eba1e82e4ca1ae85f92f6d74c31a
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812160B2

연결된 노트

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