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Methanol → 2-Amino-2-((4-(5-(6-propylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diol

HRID 710476
ノート
印刷プレビュー

反応式

HRID 710476 の反応式
CC1(C)[O:7][CH2:6][C:5]([NH:32]C(=O)OC(C)(C)C)([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([C:18]4[N:22]=[C:21]([C:23]5[CH:24]=[N:25][C:26]([CH2:29][CH2:30][CH3:31])=[CH:27][CH:28]=5)[O:20][N:19]=4)[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH2:4][O:3]1.[Na+].[I-].CO>CC#N.[Si](Cl)(C)(C)C>[NH2:32][C:5]([CH2:8][N:9]1[C:17]2[C:12](=[C:13]([C:18]3[N:22]=[C:21]([C:23]4[CH:24]=[N:25][C:26]([CH2:29][CH2:30][CH3:31])=[CH:27][CH:28]=4)[O:20][N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)([CH2:4][OH:3])[CH2:6][OH:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 887MethanolHCID 5238Sodium IodideHCID 66726785tert-Butyl 2,2-dimethyl-5-((4-(5-(6-propylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-1,3-dioxan-5-ylcarbamate

生成物 1

HCID 461958852-Amino-2-((4-(5-(6-propylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diol収率 49%

試薬・触媒・溶媒 2

HCID 6342
Acetonitrile
溶媒
HCID 6397Chlorotrimethylsilane溶媒

実験手順

To a solution of the product of Step E (0.018 g; 0.033 mmol), NaI (0.015 g; 0.0981 mmol) in anhydrous CH3CN (0.6 ml), Me3SiCl (0.08 ml) was added at room temperature with stirring under N2. After stirring for 30 min MeOH (0.5 ml) was added and solvents were removed under reduced pressure. The residue was purified by FCC (SiO2; NH4OH saturated CH2Cl2:MeOH 95:5) to give the title compound (0.0066 g; 49%) as colourless solid. 1H-NMR (CDCl3+CD3OD) 0.93 (tr, 3H, J=(Hz); 1.67-1.81 (m, 2H); 2.81 (tr, 2H, J=9 Hz); 2.99 (broad s, CD3OH); 3.07 (s, 2H); 3.26-3.65 (m, 8H); 6.74 (d, 1H, J=9 Hz); 7.15 (m, 1H); 7.31 (d, 1H, J=9 Hz); 7.42 (d, 1H, J=9 Hz); 8.32 (dd, 1H, J=3, 9 Hz); 9.33 (d, 1H, 3 Hz).

後処理

  1. additionwas added
  2. customsolvents were removed under reduced pressure
  3. customThe residue was purified by FCC (SiO2; NH4OH saturated CH2Cl2:MeOH 95:5)

出典と根拠

ORDレコード
ord-64fa259fa00841009b64293144675c67
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181182B2

反応ノート

読み込み中…

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