Triethylamine → 3-((4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)benzaldehyde

HRID 471223ノート

反応式

HRID 471223 の反応式
FC(F)(F)C(O)=O.[CH3:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([N:16]2[CH2:21][C:20]3([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[O:19][CH2:18][CH2:17]2)=[O:15])[N:13]=1.Br[CH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH:32]=[O:33].C(N(CC)CC)C>C(#N)C>[CH3:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([N:16]2[CH2:21][C:20]3([CH2:26][CH2:25][N:24]([CH2:28][C:29]4[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=4)[CH:32]=[O:33])[CH2:23][CH2:22]3)[O:19][CH2:18][CH2:17]2)=[O:15])[N:13]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 71278253-(Bromomethyl)benzaldehydeHCID 66964121(2-Methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

生成物 1

HCID 579889313-((4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)benzaldehyde

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of (2-methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 4, step h) (0.408 g), 3-(bromomethyl)benzaldehyde (0.205 g) and triethylamine (0.36 mL) in acetonitrile (10 mL) was stirred at room temperature overnight. The solution was concentrated in vacuo and the residue partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was washed twice with water, once with brine, then dried over anhydrous magnesium sulphate and purified by flash chromatography on silica eluted with 5% methanol in dichloromethane to afford the subtitled compound as a yellow gum. Yield 0.325 g.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic phase was washed twice with water, once with brine
  4. dry with materialdried over anhydrous magnesium sulphate
  5. custompurified by flash chromatography on silica
  6. washeluted with 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-ffee0de109ab45749025bb38e6c788d1
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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