Trifluoroacetic acid → (3-Aminopyridin-2-yl){1-[3-(trifluoromethyl)phenyl]cyclobutyl}methanol

HRID 1620997ノート

反応式

HRID 1620997 の反応式
[OH:1][CH:2]([C:17]1([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[CH2:20][CH2:19][CH2:18]1)[C:3]1[C:8]([NH:9]C(=O)OC(C)(C)C)=[CH:7][CH:6]=[CH:5][N:4]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:9][C:8]1[C:3]([CH:2]([C:17]2([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=3)[CH2:20][CH2:19][CH2:18]2)[OH:1])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 89524814Tert-butyl 2-(hydroxy(1-(3-(trifluoromethyl)phenyl)cyclobutyl)methyl)-pyridin-3-ylcarbamate

生成物 1

HCID 71523069(3-Aminopyridin-2-yl){1-[3-(trifluoromethyl)phenyl]cyclobutyl}methanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of Example 120D (96 mg, 0.229 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (2 mL). The resulting solution was stirred at room temperature for about 2 hours, and concentrated in vacuum. The residue was treated with saturated NaHCO3 and extracted with ethyl acetate three times. Combined organic phases were washed with water and brine sequentially, dried over Na2SO4, filtered, and concentrated. The residue was purified by prep-HPLC (Column: BOSTON-C18 20×250 mm 10 μm, eluent: water (0.05% NH4HCO3): acetonitrile, 1:1 to 5:95) (60 mg, 30%) to provide the title compound. LC-LC-MS: m/z (M+H) 323. 1H NMR (400 MHz, CDCl3): δ 7.78-7.80 (m, 1H), 7.35-6.99 (m, 4H), 6.82-6.86 (m, 1H), 6.58-6.61 (m, 1H), 4.77 (s, 1H), 3.00 (b, 3H), 2.69-2.82 (m, 2H), 2.14-2.27 (m, 2H), 1.65-1.95 (m, 2H).

後処理

  1. concentrationconcentrated in vacuum
  2. additionThe residue was treated with saturated NaHCO3
  3. extractionextracted with ethyl acetate three times
  4. washCombined organic phases were washed with water and brine sequentially
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by prep-HPLC (Column

出典と根拠

ORDレコード
ord-9ed5111f81364b7c8849868f96a07904
出典データセット
uspto-grants-2014_07
特許番号
US08772500B2

反応ノート

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