Diisopropylethylamine → HCID 59170090, compound

HRID 1446304Notes

Reaction equation

HRID 1446304 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([OH:15])=O)[CH:5]=[CH:6][CH:7]=1.[C:16]1([CH:22]2[CH2:26][CH2:25][NH:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([N:24]2[CH2:25][CH2:26][CH:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23]2)=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 31467433-PhenylpyrrolidineHCID 228317095-(3-Fluorophenyl)-1,2-oxazole-4-carboxylic acid

Product 1

HCID 59170090HCID 59170090, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3-fluorophenyl)-isoxazole-4-carboxylic acid (47.8 mg, 0.231 mmol), 3-phenylpyrrolidine (40 mg, 0.271 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (92.6 mg, 0.288 mmol) and diisopropylethylamine (49.7 mg, 0.384 mmol) were mixed in dimethylformamide (1.5 mL) and stirred at room temperature over night. Solvent was evaporated in vacuo (0.5-1.0 mL) and the residue was taken up in dichloromethane (1 mL), filtered and purified by normal-phase chromatography (20-50% EtOAc:petroleum ether). The combined fractions were partitioned between H2O/acetic acid (pH 4) and ethyl acetate. The organic fractions were washed with H2O/brine and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C20H17FN2O2: 336.1274, found 336.1277.

Workup

  1. customSolvent was evaporated in vacuo (0.5-1.0 mL)
  2. filtrationfiltered
  3. custompurified by normal-phase chromatography (20-50% EtOAc:petroleum ether)
  4. customThe combined fractions were partitioned between H2O/acetic acid (pH 4) and ethyl acetate
  5. washThe organic fractions were washed with H2O/brine
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a772e1895604efa84ff9a1ede875d31
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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