Ammonium Chloride → HCID 178424147, compound

HRID 533285Notes

Reaction equation

HRID 533285 reaction equation
C[N:2]1[C:6]([C:7]2[N:8]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29][CH:28]=3)[C:9]3[C:14]([CH:15]=2)=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH:12]=[CH:11][CH:10]=3)=CC(O)=N1.[N-:38]=[N+:39]=[N-:40].[Na+].[NH4+].[Cl-]>CN(C)C=O>[CH3:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[CH:15]=[C:7]([C:6]1[NH:2][N:40]=[N:39][N:38]=1)[N:8]2[CH2:23][CH2:24][CH2:25][O:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 178424146HCID 178424146, compound

Product 1

HCID 178424147HCID 178424147, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of EXAMPLE 168B (416 mg) in N,N-dimethylformamide (10 ml) was added NaN3 (281 mg) and NH4Cl (231 mg). The mixture was stirred at reflux overnight. After this time the mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate (200 ml) and water (60 ml). The organic phase was washed with brine and dried over Na2SO4. After concentration of solvent, the residue was dissolved in dimethylsulfoxide/methanol(1:1, 2 ml) and purified via RPHPLC. 1H NMR (300 MHz, DMSO-d6) δ 8.24 (m, 1H), 7.88 (m, 1H), 7.54 (m, 3H), 7.47 (d, 1H), 7.40 (d, 1H), 7.30 (m, 5H), 7.14 (t, 1H), 6.88 (d, 2H), 6.23 (s, 1H), 5.70 (s, 1H), 4.91 (m, 2H), 4.21 (m, 2H), 3.51 (m, 3H), 2.36 (m, 2H), 2.14 (s, 3H).

Workup

  1. temperatureat reflux overnight
  2. concentrationAfter this time the mixture was concentrated under vacuum
  3. customthe residue was partitioned between ethyl acetate (200 ml) and water (60 ml)
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. dissolutionAfter concentration of solvent, the residue was dissolved in dimethylsulfoxide/methanol(1:1, 2 ml)
  7. custompurified via RPHPLC

Sources & evidence

ORD record
ord-f6a04150d642402e92ba30ab8cfb9fe6
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

Loading…