Triethylamine → HCID 86596775, compound

HRID 917016Notes

Reaction equation

HRID 917016 reaction equation
[CH:1]1([CH2:4][O:5][NH:6][C:7]([C:9]2[C:10]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=3[Cl:28])=[C:11]([F:19])[C:12]3[O:16][N:15]=[C:14]([CH3:17])[C:13]=3[CH:18]=2)=[O:8])CC1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[CH:46]([O:48]CCON)=[CH2:47].CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[CH:46]([O:48][CH2:1][CH2:4][O:5][NH:6][C:7]([C:9]1[C:10]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=2[Cl:28])=[C:11]([F:19])[C:12]2[O:16][N:15]=[C:14]([CH3:17])[C:13]=2[CH:18]=1)=[O:8])=[CH2:47]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11511107HCID 11511107, compoundHCID 21867017O-(2-(Vinyloxy)ethyl)hydroxylamine

Product 1

HCID 86596775HCID 86596775, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methylbenzo [d]isoxazole-5-carboxylic acid (10a) (75.2 mg, 0.188 mmol) in DMF (1.5 mL) was added HOBt (38.2 mg, 0.249 mmol), Et3N (0.080 mL, 0.571 mmol), O-(2-vinyloxyethyl)hydroxylamine (28.5 mg, 0.276 mmol), and EDCI (47.2 mg, 0.246 mmol) at room temperature. After 6 days, the reaction mixture was diluted with EtOAc, washed with saturated aqueous NH4Cl, brine, saturated aqueous NaHCO3, and brine. The organic layer was dried over MgSO4, filtered, concentrated in vacuo, and purified by flash column chromatography using the Biotage system (3% MeOH in CH2Cl2) to give 57.8 mg (63%) of the desired product (11a).

Workup

  1. washwashed with saturated aqueous NH4Cl, brine, saturated aqueous NaHCO3, and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-0b931f641eea422799a2a8eeca1c7a6e
Source dataset
uspto-grants-2007_09
Patent number
US07271178B2

Reaction notes

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