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

HRID 2422164

反応式

HRID 2422164 の反応式
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:6]([CH3:24])=[N:7][C:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[N:9][C:10]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]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>[CH3:24][C:6]1[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:25])=[C:10]([N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[N:9]=[C:8]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][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:21][CH:22]=2)[N:7]=1

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d80c2ccf90c94b66aad6df796da19011
出典データセット
uspto-grants-2011_06
特許番号
US07960393B2

関連ノート

読み込み中…