HCID 123831591, compound → HCID 67418106, compound

HRID 571044Notes

Reaction equation

HRID 571044 reaction equation
C(OC(=O)[NH:7][C:8]1[N:9]([C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:26]=[CH:27][CH:28]=2)[CH:10]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](=[O:14])[CH:13]=1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:7][C:8]1[N:9]([C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:26]=[CH:27][CH:28]=2)[CH:10]=[C:11]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12](=[O:14])[CH:13]=1

Participants

3

Reactant 1

HCID 123831591HCID 123831591, compound

Product 1

HCID 67418106HCID 67418106, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

To tert-butyl[5-(benzyloxy)-1-(biphenyl-3-yl)-4-oxo-1,4-dihydropyridin-2-yl]carbamate (4.68 g, 10 mmol) was added TFA-DCM (1:1, 60 mL), and the resulting solution was stirred for 1 h at rt. The solution was then concentrated and treated with saturated aq. NaHCO3-EtOAc. The organic layer was separated, washed with brine, dried (Na2SO4), filtered, and concentrated to give 2-amino-5-(benzyloxy)-1-(biphenyl-3-yl)pyridin-4(1H)-one as a slightly yellow solid 1H NMR (500 MHz, DMSO): ä 7.82 (ddd, J=7.8, 1.8, 1.0 Hz, 1 H); 7.76-7.73 (m, 2 H); 7.67-7.61 (m, 2 H); 7.53-7.47 (m, 2 H); 7.43-7.34 (m, 6 H); 7.33-7.29 (m, 1 H); 7.04 (s, 1 H); 5.65 (s, 2 H); 5.49 (s, 1 H); 4.89 (s, 2 H).

Workup

  1. concentrationThe solution was then concentrated
  2. additiontreated with saturated aq. NaHCO3-EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-15b1ce93c66e4fac83980e50a3b34158
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

Loading…