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

HRID 577983Notes

Reaction equation

HRID 577983 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-0b4b1d40b9364a90b234cef80e703a5d
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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