Ammonium Chloride → HCID 58338347, compound

HRID 1877509Notes

Reaction equation

HRID 1877509 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.OC1C2N=NNC=2C=CC=1.[Cl-].[NH4+].C(N(C(C)C)CC)(C)C.[C:49]([C:51]1[N:56]=[CH:55][C:54]([C:57]2[C:69]3[C:68]4[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=4)[N:62]([C:70]4[CH:78]=[CH:77][C:73]([C:74]([OH:76])=O)=[C:72]([NH:79][CH2:80][CH2:81][C:82]([OH:85])([CH3:84])[CH3:83])[CH:71]=4)[C:61]=3[CH:60]=[CH:59][CH:58]=2)=[CH:53][CH:52]=1)#[N:50]>CN(C)C=O.O>[C:49]([C:51]1[N:56]=[CH:55][C:54]([C:57]2[C:69]3[C:68]4[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=4)[N:62]([C:70]4[CH:78]=[CH:77][C:73]([C:74]([NH2:8])=[O:76])=[C:72]([NH:79][CH2:80][CH2:81][C:82]([OH:85])([CH3:83])[CH3:84])[CH:71]=4)[C:61]=3[CH:60]=[CH:59][CH:58]=2)=[CH:53][CH:52]=1)#[N:50]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67308714HCID 67308714, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 58338347HCID 58338347, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

108 mg of (1H-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (BOP), 33 mg of hydroxybenzotriazole (HOBT), 17 mg of ammonium chloride and 0.1 ml of diisopropylethylamine are successively added to a solution of 80 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxy-3-methylbutyl)amino]benzoic acid in 10 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 12 hours and then diluted with distilled water and extracted with ethyl acetate. The organic phase is subsequently washed with distilled water and a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of dichloromethane and methanol (96/4 by volume), so as to give 18 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxy-3-methylbutyl)amino]benzamide in the form of a white solid, the characteristics of which are the following:

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is subsequently washed with distilled water
  3. dry with materiala saturated solution of sodium chloride, dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography, elution
  7. additionbeing carried out with a mixture of dichloromethane and methanol (96/4 by volume)

Sources & evidence

ORD record
ord-7159da633e964c418b9266374817489b
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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