2-Chlorobenzoxazole → HCID 23121962, compound

HRID 1713514Notes

Reaction equation

HRID 1713514 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.Cl[C:33]1[O:34][C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=1>O1CCCC1>[O:34]1[C:35]2[CH:41]=[CH:40][CH:39]=[CH:38][C:36]=2[N:37]=[C:33]1[N:13]1[CH2:14][CH2:15][N:10]2[C:9](=[O:16])[O:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:11]2[CH2:12]1

Participants

5

Reactant 3

HCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 23121962HCID 23121962, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (60 mg, 0.2 mmol) in tetrahydrofuran (2 mL) were sequentially added diisopropylethylamine (0.3 mL) and 2-chlorobenzoxazole (45 mg, 0.29 mmol), and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure. Then, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1) and recrystallized from diisopropyl ether to obtain the title compound (51 mg, yield 62%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThen, the residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1)
  3. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-1cd5431f046b41caa83c8a74358ce6ec
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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