2-Aminoindane → HCID 58276358, 화합물

HRID 70337노트

반응식

HRID 70337 반응식
[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=O)[CH:19]=3)=[CH:14][CH:13]=2)=[N:8]1)=[O:4].[NH2:28][CH:29]1[CH2:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30]1.C1COCC1.CO>C(O)(=O)C>[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]([O:5][CH2:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH:28][CH:29]4[CH2:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:30]4)[CH:19]=3)=[CH:16][CH:17]=2)=[N:8]1)=[O:4]

참가 물질

5

반응물 3

HCID 763102-AminoindaneHCID 21899815MeOH tetrahydrofuranHCID 58276410HCID 58276410, 화합물

생성물 1

HCID 58276358HCID 58276358, 화합물

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of [3-(3′-formyl-4-biphenylyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethylpropanoate (0.081 g, 0.22 mmol; I-X-17) and 2-aminoindane (0.045 mL, 0.35 mmol) in 1:1 THF/MeOH (2 mL) was added acetic acid (0.12 mL) and MP—BH3CN (ca. 0.67 mmol, Note 1). The mixture was stirred at room temperature overnight, resin was remove by filtration (THF wash) and the filtrate was concentrated in vacuo. The residue was partitioned between EtOAc/5% Na2CO3, layers were separated and the aqueous layer was extracted with EtOAc. Combined organics were washed (water, brine), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography (MeOH/CH2Cl2), affording the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.20 (s, 9 H), 2.84 (dd, J=15.6, 6.4 Hz, 2 H), 3.20 (dd, J=15.6, 7.1 Hz, 2 H), 3.68-3.75 (m, 1 H), 3.93 (s, 2 H), 6.09 (s, 2 H), 7.08-7.23 (m, 4 H), 7.31-7.38 (m, 1 H), 7.41 (t, J=7.6 Hz, 1 H), 7.53 (d, J=7.6 Hz, 1 H), 7.63 (s, 1 H), 7.69 (d, J=8.3 Hz, 2 H), 8.19 (d, J=8.3 Hz, 2 H), 8.37 (s, 1 H).

후처리

  1. customresin was remove by filtration (THF wash)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between EtOAc/5% Na2CO3, layers
  4. customwere separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washCombined organics were washed (water, brine)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-73dbbbf537394ce184ea6d8a98a5a143
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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