Ammonium Chloride → HCID 178424148, compound

HRID 2095293Notes

Reaction equation

HRID 2095293 reaction equation
COC1C=CC(C[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH3:23])[C:10]([CH2:24][CH2:25][CH2:26][O:27][C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)=[C:9]2[C:38]#[N:39])=CC=1.[N-:42]=[N+:43]=[N-:44].[Na+].[NH4+].[Cl-]>C[N-]C.ClCCl.FC(F)(F)C(O)=O>[CH3:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[NH:8][C:9]([C:38]1[NH:39][N:44]=[N:43][N:42]=1)=[C:10]2[CH2:24][CH2:25][CH2:26][O:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68934133HCID 68934133, compound

Product 1

HCID 178424148HCID 178424148, compound

Reagents, catalysts & solvents 2

HCID 182180DimethylazanideSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Conditions

Temperature
125 °C

Procedure

To a mixture of EXAMPLE 581D (232 mg) in N, N-dimethylamide (10 ml) was added NaN3 (281 mg) and NH4Cl (231 mg). The mixture was stirred at reflux overnight. 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. Concentration of the solvent gave crude product which was dissolved in dichloromethane/trifluoroacetic acid (1:1, 4 ml) and heated to 125° C. in a microwave (CEM Discover) for 20 minutes. The mixture was concentrated and the residue was dissolved in dimethylsulfoxide/methanol (1/1, 2 ml) and loaded on HPLC for purification. 1H NMR (300 MHz, DMSO-d6) δ 10.63 (m, 1H), 8.26 (m, 1H), 7.86 (m, 1H), 7.74 (d, 1H), 7.53 (m, 2H), 7.42 (m, 5H), 7.33 (m, 2H), 7.11 (m, 3H), 6.90 (d, 1H), 4.23 (t, 2H), 2.29 (m, 2H), 2.13 (s, 3H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe 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. customConcentration of the solvent gave crude product which
  7. concentrationThe mixture was concentrated
  8. dissolutionthe residue was dissolved in dimethylsulfoxide/methanol (1/1, 2 ml)
  9. customloaded on HPLC for purification

Sources & evidence

ORD record
ord-51e4dfb8825d49a8951b33a5e245b99b
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

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