Potassium bis(trimethylsilyl)amide → [3-(3-Methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester

HRID 1823273ノート

反応式

HRID 1823273 の反応式
[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19]([C:21]2[C:22]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][C:28]=3F)=[N:23][O:24][C:25]=2[CH3:26])=[O:20])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]2[C:32]3[C:27](=[CH:28][CH:29]=[N:30][CH:31]=3)[C:22]3=[N:23][O:24][C:25]([CH3:26])=[C:21]3[C:19]2=[O:20])[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 69652630HCID 69652630、化合物

生成物 1

HCID 69652694[3-(3-Methyl-4-oxo-5H-2-oxa-1,5,7-triaza-cyclopenta[a]naphthalen-5-yl)-cyclohexylmethyl]-carbamic acid benzyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Dissolve (3-{[3-(3-fluoro-pyridin-4-yl)-5-methyl-isoxazole-4-carbonyl]-amino}-cyclohexylmethyl)-carbamic acid benzyl ester (0.65 g, 0.0014 mol) in N,N-dimethylformamide (6 mL) at ambient temperature under a nitrogen atmosphere. Add a solution of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 3.35 mL, 0.0017 mol) and stir for 15 min. at ambient temperature. Quench the dark mixture with water and follow with the addition of solid sodium chloride. Extract with ethyl acetate and wash the combined extracts with water and dry over sodium sulfate. Concentrate and elute over silica gel with methanol/dichloromethane allowing for the isolation of 0.44 g (71%) of the desired product as an off white solid. MS(S): (M+1)+ 447.2, 448.2 m/z.

後処理

  1. customQuench the dark mixture with water
  2. additionfollow with the addition of solid sodium chloride
  3. extractionExtract with ethyl acetate
  4. washwash the combined extracts with water
  5. dry with materialdry over sodium sulfate
  6. concentrationConcentrate
  7. washelute over silica gel with methanol/dichloromethane allowing for the isolation of 0.44 g (71%) of the desired product as an off white solid

出典と根拠

ORDレコード
ord-18ef72f08d0f40ce8a1b68d41f6c6f0a
出典データセット
uspto-grants-2006_05
特許番号
US07037921B2

反応ノート

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