Triethylamine → (9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-(trifluoromethyl)thiazol-4-yl)methanone

HRID 471024노트

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HRID 471024 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.[O:19]1[C:24]2([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][N:22]([C:30]([C:32]2[N:33]=[C:34]([C:37]([F:40])([F:39])[F:38])[S:35][CH:36]=2)=[O:31])[CH2:21][CH2:20]1.C(N(CC)CC)C>C(#N)C>[OH:11][CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][N:27]1[CH2:28][CH2:29][C:24]2([O:19][CH2:20][CH2:21][N:22]([C:30]([C:32]3[N:33]=[C:34]([C:37]([F:38])([F:39])[F:40])[S:35][CH:36]=3)=[O:31])[CH2:23]2)[CH2:25][CH2:26]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18999576Benzeneethanol, 3-(bromomethyl)-HCID 866367511-Oxa-4,9-diazaspiro[5,5]undecan-4-yl(2-(trifluoromethyl)thiazol-4-yl)methanone trifluoroacetate

생성물 1

HCID 57989285(9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-(trifluoromethyl)thiazol-4-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) (0.354 g) was added to a solution of 1-oxa-4,9-diazaspiro[5.5]undecan-4-yl(2-(trifluoromethyl)thiazol-4-yl)methanone trifluoroacetate (example 25, step a) (0.74 g) and triethylamine (0.689 mL) in acetonitrile (15 mL) and the mixture stirred at 20° C. for 2 hours. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution, 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 1% triethylamine and 3% methanol in dichloromethane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.640 g.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  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-1fe860fdfd634c2b9fc5ec183803ce2f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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