Acetic Acid → HCID 44124557、化合物

HRID 1045361ノート

反応式

HRID 1045361 の反応式
[OH:1][C:2]1([C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH3:17][O:18][CH2:19][C:20]1([C:25]([N:27]2[CH2:36][CH2:35][C:34]3[N:33]=[CH:32][C:31]([C:37]([F:40])([F:39])[F:38])=[CH:30][C:29]=3[CH2:28]2)=[O:26])[CH2:24][CH2:23][NH:22][CH2:21]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(OCC)(=O)C>[OH:1][C:2]1([C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[CH2:7][CH2:6][CH:5]([N:22]2[CH2:23][CH2:24][C:20]([C:25]([N:27]3[CH2:36][CH2:35][C:34]4[N:33]=[CH:32][C:31]([C:37]([F:39])([F:38])[F:40])=[CH:30][C:29]=4[CH2:28]3)=[O:26])([CH2:19][O:18][CH3:17])[CH2:21]2)[CH2:4][CH2:3]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 529879954-Hydroxy-4-(6-methoxypyridin-3-YL)cyclohexanoneHCID 59569566HCID 59569566、化合物

生成物 1

HCID 44124557HCID 44124557、化合物

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The title compound was prepared according to general procedures described in Scheme 2: A mixture of 4-hydroxy-4-(6-methoxypyridin-3-yl)cyclohexanone (71 mg, 0.32 mmol), (3-(methoxymethyl)pyrrolidin-3-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone VIc (100 mg, 0.29 mmol) and acetic acid (20 μL, 0.34 mmol) in dichloroethane (3 mL) was stirred at room temperature for 0.5 h. Sodium triacetoxyborohydride (123 mg, 0.576 mmol) was added and the reaction mixture was stirred for 2 h at room temperature. After concentration of solvent under reduced pressure, the resulting residue was dissolved in ethyl acetate, then washed with NaHCO3, water and brine. The organic extract was dried, filtered and concentrated. The crude product was obtained as a mixture of isomers which were further separated by reverse phase preparative HPLC to yield isomer A (eluted at 10.092 min) and isomer B (eluted at 11.269 min).

後処理

  1. stirringthe reaction mixture was stirred for 2 h at room temperature
  2. washwashed with NaHCO3, water and brine
  3. extractionThe organic extract
  4. customwas dried
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-6ed87c0d32184f9894cffe87565e1073
出典データセット
uspto-grants-2013_10
特許番号
US08569282B2

反応ノート

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