Dimethylformamide → HCID 59170048, compound

HRID 1446271Notes

Reaction equation

HRID 1446271 reaction equation
[C:1]1([CH:7]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14]([OH:16])=O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)C(C)C)C.Cl.[C:27]1([CH:33]2[CH2:37][CH2:36][NH:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CN(C=[O:42])C>>[C:27]1([C:33]2([OH:42])[CH2:37][CH2:36][N:35]([C:14]([C:10]3[CH:11]=[N:12][O:13][C:9]=3[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH3:8])=[O:16])[CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 441188043-Phenylpyrrolidine--hydrogen chloride (1/1)HCID 68683173HCID 68683173, compound

Product 1

HCID 59170048HCID 59170048, compound

Procedure

A solution of 5-(1-phenylethyl)isoxazole-4-carboxylic acid (11 mg, 0.05 mmol) TBTU (19 mg, 0.06 mmol, 1,2 equ.) and N-ethyl-N-isopropylpropan-2-amine (26 μL, 0.15 mmol, 3 equ) in DMF (0.3 mL) was added to 3-phenylpyrrolidine hydrochloride (10 mg, 0.05 mmol) and the reaction mixture was left at rt for 2 h. The solvent was evaporated and the crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (5 mg). MS (ESI, pos. ion) m/z calcd for C22H22N2O3: 362.1630, found 362.1627.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by RP-HPLC
  3. customAfter evaporation of the solvents the product
  4. customwas dried in vacuum

Sources & evidence

ORD record
ord-a7709d7d2b4046288fc9270c2ce9c5a3
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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