Benzyl Bromide → HCID 58424109, compound

HRID 1408777Notes

Reaction equation

HRID 1408777 reaction equation
[NH2:1][C:2]1[N:3]([CH3:23])[O:4][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:16])[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1.Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:25]([O:16][C:13]1[CH:14]=[C:15]2[C:5]3([O:4][N:3]([CH3:23])[C:2]([NH2:1])=[N:6]3)[CH2:7][CH:8]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:9][C:10]2=[CH:11][CH:12]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58423904HCID 58423904, compound

Product 1

HCID 58424109HCID 58424109, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3′amino-2′-methyl-2-phenyl-2′H-spiro(chroman-4,5′-(1,2,4)oxadiazol)-6-ol (30 mg, 0.096 mmol), (bromomethyl)benzene (21.45 mg, 0.125 mmol) and K2CO3 (16 mg, 0.115 mmol) was dissolved in acetone, then the mixture was stirred at room temperature for 24 hours. The mixture was filtrated and concentrated. The residue was purified by preparative HPLC to give 6-(benzyloxy)-2′-methyl-2-phenyl-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (140) (0.95 mg, 3%). 1H-NMR (MeOD): 7.32-7.56 (m, 10H), 6.91-7.23 (m, 3H), 5.12 (d, 2H), 5.23 (t, 2H), 3.31 (s, 3H) 2.73 (m, 1H), 2.32 (m, 1H);

Workup

  1. filtrationThe mixture was filtrated
  2. concentrationconcentrated
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f59793485f0d4e119563186b347141b6
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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