Hydrochloric Acid → HCID 46847289, compound

HRID 415195Notes

Reaction equation

HRID 415195 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([OH:19])=O)[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1.C1C=CC2N(O)N=[N:26]C=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[Cl-].[NH4+].Cl>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([NH2:26])=[O:19])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66621013HCID 66621013, compound

Product 1

HCID 46847289HCID 46847289, compoundYield 4.15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(4-bromophenyl)benzo[d]oxazole-4-carboxylic acid (0.075 g, 0.24 mmol) in dimethyl formamide (10 mL) was added HOBT (0.0425 g, 0.28 mmol), EDCI (0.0575 g, 0.3 mmol), DIPEA (0.097 g, 0.75 mmol) and ammonium chloride (0.0133 g, 0.25 mmol). The reaction mixture was stirred at room temperature for 20 hr, cooled and poured into water (10 mL). The solution was acidified to pH=3 with 1N aqueous hydrochloric acid. Then the solution was extracted with dichloromethane (70 mL×3). The organic layer was washed with brine, dried over anhydrous sodium sulfate, condensed in vacuum and separated by silica gel chromatography (ethyl acetate:methanol=1:0 to 10:1) to afford 2-(4-bromophenyl)benzo[d]oxazole-4-carboxamide as a solid (0.003 g, yield 4.15%). LC-MS (ESI) m/z 319 [M+1]+.

Workup

  1. temperaturecooled
  2. extractionThen the solution was extracted with dichloromethane (70 mL×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate, condensed in vacuum
  5. customseparated by silica gel chromatography (ethyl acetate:methanol=1:0 to 10:1)

Sources & evidence

ORD record
ord-999c29bbf6b94e738ebc2613f2538bd9
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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