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

HRID 1620997노트

반응식

HRID 1620997 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9ed5111f81364b7c8849868f96a07904
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772500B2

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