Tetrahydrofuran → HCID 52918969, compound

HRID 1846079Notes

Reaction equation

HRID 1846079 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=2[F:17])=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:31]([C:33]([CH3:36])([CH3:35])[CH3:34])=[O:32])=[CH:25][C:21]=1[C:22](O)=[O:23].C1COCC1>CN(C=O)C>[F:17][C:11]1[CH:12]=[CH:13][C:14]([NH:16][C:22](=[O:23])[C:21]2[CH:25]=[C:26]([CH2:29][NH:30][C:31]([C:33]([CH3:34])([CH3:36])[CH3:35])=[O:32])[CH:27]=[CH:28][C:20]=2[Cl:19])=[CH:15][C:10]=1[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)=[O:18]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 43510731HCID 43510731, compoundHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acid

Product 1

HCID 52918969HCID 52918969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

PPA (0.142 mL 50% solution in DMF) was added dropwise to a mixture of N-(4-bromophenyl)-2-fluoro-5-amino-benzoic acid amide (57 mg, 0.19 mmol), 2-chloro-5-(tert-butylcarbonylamino)methyl-benzoic acid (50 mg, 0.19 mmol), 64 μL TEA and 10 mL THF. The reaction was refluxed overnight, additional PPA (0.14 mL) was added and it was refluxed for additional 4.5 h. The crude reaction mixture was concentrated i.vac., EtOAc was added and the organic phase was washed with 2 M aq. HCl, satd. NaHCO3, dried with Na2SO4 and purified via HPLC (Method A) to furnish the title compound.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. additionadditional PPA (0.14 mL) was added
  3. temperatureit was refluxed for additional 4.5 h
  4. customThe crude reaction mixture
  5. concentrationwas concentrated i.vac
  6. addition, EtOAc was added
  7. washthe organic phase was washed with 2 M aq. HCl
  8. dry with materialNaHCO3, dried with Na2SO4
  9. custompurified via HPLC (Method A)

Sources & evidence

ORD record
ord-65c53d787fe042a8a6a24c2352fc6e0b
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

Loading…