Triethylamine → (2,2-Difluoro-9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

HRID 1689284노트

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HRID 1689284 반응식
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1.FC(F)(F)C(O)=O.[F:19][C:20]1([F:39])[CH2:25][N:24]([C:26]([C:28]2[S:29][C:30]([CH3:33])=[CH:31][CH:32]=2)=[O:27])[CH2:23][C:22]2([CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[O:21]1.C(N(CC)CC)C>C(#N)C>[F:39][C:20]1([F:19])[CH2:25][N:24]([C:26]([C:28]2[S:29][C:30]([CH3:33])=[CH:31][CH:32]=2)=[O:27])[CH2:23][C:22]2([CH2:34][CH2:35][N:36]([CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH2:10][OH:11])[CH:4]=3)[CH2:37][CH2:38]2)[O:21]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 67291912(2,2-Difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone trifluoroacetate

생성물 1

HCID 57989272(2,2-Difluoro-9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
20 °C

실험 절차

2-(3-(Bromomethyl)phenyl)ethanol (example 6, step a) (0.095 g) was added to a solution of (2,2-difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone trifluoroacetate (example 37, step e) (0.19 g) and triethylamine (0.185 mL) in acetonitrile (10 mL) and the reaction mixture stirred at 20° C. for 3 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and brine, the organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 2.5% methanol in dichloromethane with 1% triethylamine as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.188 g.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and brine
  3. dry with materialthe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-4dedb73dfc8b4683a5bf1d6cdcd3ac69
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148373B2

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