Benzaldehyde → {3-(benzylamino)-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzoxazol-5-yl}methanol

HRID 245523

反応式

HRID 245523 の反応式
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.[NH2:16][C:17]1[C:21]2[CH:22]=[C:23]([CH2:35][OH:36])[C:24]([N:27]3[CH2:32][C@H:31]([CH3:33])[O:30][C@H:29]([CH3:34])[CH2:28]3)=[C:25]([F:26])[C:20]=2[O:19][N:18]=1>C(O)(C(F)(F)F)=O>[CH2:1]([NH:16][C:17]1[C:21]2[CH:22]=[C:23]([CH2:35][OH:36])[C:24]([N:27]3[CH2:32][C@H:31]([CH3:33])[O:30][C@H:29]([CH3:34])[CH2:28]3)=[C:25]([F:26])[C:20]=2[O:19][N:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 12052TriethylsilaneHCID 67359017{3-amino-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzisoxazol-5-yl}methanol2 回

生成物 1

HCID 67356861{3-(benzylamino)-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzoxazol-5-yl}methanol

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To an ice cooled solution of benzaldehyde (0.08 mL, 2.54 mmol) in TFA (5 mL) was added triethylsilane (0.4 mL, 2.5 mmol) followed by {3-amino-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzisoxazol-5-yl}methanol (Intermediate 7, 250 mg, 0.84 mmol), and slowly allowed to reach room temperature and stirred for 12 hour. The reaction mixture was concentrated and the residue thus obtained was purified column chromatography using EtOAc in petether to give the title compound as solid. Yield: 70 mg (21%).

後処理

  1. customto reach room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue thus obtained
  4. customwas purified column chromatography

出典と根拠

ORDレコード
ord-b6262d6f6aba4d798c04da0999b73e5f
出典データセット
uspto-grants-2014_02
特許番号
US08658641B2

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