Ammonium Chloride → HCID 178424147, compound

HRID 1013326Notes

Reaction equation

HRID 1013326 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-707c202c870b41399d1f876d5444e712
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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