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

HRID 245523

반응식

HRID 245523 반응식
[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

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 12052TriethylsilaneHCID 67359017{3-amino-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzisoxazol-5-yl}methanol2회

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-b6262d6f6aba4d798c04da0999b73e5f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658641B2

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