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

HRID 471024ノート

反応式

HRID 471024 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 57989285(9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-(trifluoromethyl)thiazol-4-yl)methanone

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1fe860fdfd634c2b9fc5ec183803ce2f
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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