Diisopropylethylamine → 3-(3,3-difluoroazetidine-1-carbonyl)-6-((2R,6R)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-5-carbaldehyde

HRID 577941ノート

反応式

HRID 577941 の反応式
C(N(C(C)C)CC)(C)C.[CH3:10][C@H:11]1[O:16][C@H:15]([CH3:17])[CH2:14][NH:13][CH2:12]1.[F:18][C:19]1([F:38])[CH2:22][N:21]([C:23]([C:25]2[C:29]3[CH:30]=[C:31]([CH:36]=[O:37])[C:32](F)=[C:33]([F:34])[C:28]=3[O:27][N:26]=2)=[O:24])[CH2:20]1>C(#N)C.O.[Cl-].[Na+].O>[F:38][C:19]1([F:18])[CH2:20][N:21]([C:23]([C:25]2[C:29]3[CH:30]=[C:31]([CH:36]=[O:37])[C:32]([N:13]4[CH2:14][C@@H:15]([CH3:17])[O:16][C@H:11]([CH3:10])[CH2:12]4)=[C:33]([F:34])[C:28]=3[O:27][N:26]=2)=[O:24])[CH2:22]1

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 11137133trans-2,6-DimethylmorpholineHCID 866580973-(3,3-Difluoroazetidine-1-carbonyl)-6,7-difluorobenzo[d]isoxazole-5-carbaldehyde2 回

生成物 1

HCID 866580983-(3,3-difluoroazetidine-1-carbonyl)-6-((2R,6R)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-5-carbaldehyde

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Diisopropylethylamine (1.432 ml, 8.20 mmol) and (2R,6R)-2,6-dimethylmorpholine (1.027 ml, 8.20 mmol) were added to a solution of 3-(3,3-difluoroazetidine-1-carbonyl)-6,7-difluorobenzo[d]isoxazole-5-carbaldehyde (Intermediate 241, 1.906 g, 6.31 mmol) in acetonitrile (50 ml). The reaction was stirred at reflux for 20 hours. The reaction was cooled to room temp, diluted with water and brine and extracted twice with ethyl acetate. The organic layers were combined, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography using a gradient of DCM to ethyl acetate. Fractions were combined and concentrated to give the title compound.

後処理

  1. temperatureat reflux for 20 hours
  2. extractionextracted twice with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-bb33a86647eb4bb2903e5b36ae2f9951
出典データセット
uspto-grants-2015_05
特許番号
US09040528B2

反応ノート

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