2-Chlorobenzoxazole → HCID 46209238, compound

HRID 1020386Notes

Reaction equation

HRID 1020386 reaction equation
[N:1]1([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[O:21][C:20]([N:22]4[CH2:27][CH2:26][CH:25]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH2:24][CH2:23]4)=[N:19][C:18]=3[C:34]([F:37])([F:36])[F:35])=[O:16])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.ClC1[O:49][C:50]2[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=2[N:52]=1>CN(C=O)C>[O:49]1[C:50]2[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=2[N:52]=[C:5]1[N:4]1[CH2:3][CH2:2][N:1]([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[O:21][C:20]([N:22]4[CH2:23][CH2:24][CH:25]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH2:26][CH2:27]4)=[N:19][C:18]=3[C:34]([F:36])([F:35])[F:37])=[O:16])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 67391802HCID 67391802, compound

Product 1

HCID 46209238HCID 46209238, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound C-18 was prepared by the general procedure for compound 84. Compound C-18 (150 mg, 0.30 mmol), Hunigs base (78 mg, 0.10 mL, 0.60 mmol), and 2-chlorobenzoxazole (92 mg, 0.60 mmol) in dry DMF (3 mL) was heated at 100° C. for 24 h. The reaction mixture was cooled and concentrated. Water (15 mL) was added, and the aqueous solution was extracted with CH2Cl2. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by silica gel chromatography (eluant:10-30% EtOAc—CH2Cl2) gave the product 236 (77 mg, 42% yield) as a beige foam.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. additionWater (15 mL) was added
  4. extractionthe aqueous solution was extracted with CH2Cl2
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (eluant:10-30% EtOAc—CH2Cl2)

Sources & evidence

ORD record
ord-8e407fbedaa645ab952191d3afce87bd
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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