Pyrrolidine → 3,3,3-Trifluoro-2-hydroxy-2-methyl-N-[4-(1-pyrrolidinylsulfonyl)phenyl]propanamide

HRID 1938168노트

반응식

HRID 1938168 반응식
[F:1][C:2]([F:20])([F:19])[C:3]([OH:18])([CH3:17])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](F)(=[O:15])=[O:14])=[CH:9][CH:8]=1)=[O:5].[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1.N1(C2C=CN=CC=2)CCCC1>C(#N)C.O>[F:1][C:2]([F:20])([F:19])[C:3]([OH:18])([CH3:17])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)=[O:5]

참가 물질

6

반응물 3

HCID 31268PyrrolidineHCID 755674-PyrrolidinopyridineHCID 105914083,3,3-trifluoro-N-(4-flurosulfonylphenyl)-2-hydroxy-2-methylpropanamide

생성물 1

HCID 98854953,3,3-Trifluoro-2-hydroxy-2-methyl-N-[4-(1-pyrrolidinylsulfonyl)phenyl]propanamide수율 92.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
22 °C

실험 절차

A solution of 3,3,3-trifluoro-N-(4-flurosulfonylphenyl)-2-hydroxy-2-methylpropanamide (0.25 g), pyrrolidine (0.28 g), and 4-pyrrolidinopyridine (12 mg) in dry acetonitrile (3 ml) was heated at reflux for 24 hours. After cooling to 22° C., the reaction mixture was diluted with water (25 ml) and extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with 1N HCl, brine, dried (Na2SO4) and evaporated to give an oil which crystallized upon suspension in hexane to yield the title compound as an off-white crystalline solid (0.27 g); mp 183°-186° C.; MS: m/z=367(M+1); NMR: 1.59 (s,3), 1.62 (m,4), 3.12 (m,4), 7.56 (s,1), 7.75-7.77 (m,2), 8.00-8.03 (m,2), 10.40 (s,1). Analysis for C14H17F3N2O4S: Calculated: C, 45.89; H, 4.68; N, 7.65; Found: C, 45.98; H, 4.76; N, 7.56.

후처리

  1. temperatureat reflux for 24 hours
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. washThe combined organic extracts were washed with 1N HCl, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give an oil which
  7. customcrystallized upon suspension in hexane

출처 및 근거

ORD 기록
ord-32d74badd89e4e6bbd9bd83ff880776a
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05693639

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