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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
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HRID 710476 반응식
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]
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6342
Acetonitrile
용매
HCID 6397Chlorotrimethylsilane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-64fa259fa00841009b64293144675c67
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181182B2

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