Ammonium Chloride → HCID 68289689, compound

HRID 878753Notes

Reaction equation

HRID 878753 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[N:12]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=1)[S:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([O-:22])=O)=[CH:18][CH:17]=1)(=[O:15])=[O:14].[Na+].[Cl-].[NH4+].C([N:43](CC)C(C)C)(C)C.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[N:12]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:33]([F:35])([F:36])[F:34])=[CH:28][CH:27]=1)[S:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH2:43])=[O:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 68289387HCID 68289387, compoundHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium

Product 1

HCID 68289689HCID 68289689, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of sodium 4-({(4-methylisoquinolin-3-yl)[4-(trifluoromethoxy)-benzyl]amino}sulfonyl)benzoate (100 mg, 0.186 mmol) prepared in Example 2, ammonium chloride (50 mg, 0.929 mmol) and N,N-diisopropylethylamine (162 μL, 0.929 mmol) in N,N-dimethylacetamide (1.8 mL) was added 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate methanaminium (85 mg, 0.223 mmol) at 0° C., and the mixture was stirred at room temperature overnight. To the reaction solution was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, washed with water twice, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0→91:9) to give 4-({(4-methylisoquinolin-3-yl)[4-(trifluoromethoxy)benzyl]amino}sulfonyl)benzamide (26 mg, 27%) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washwashed with water twice
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0→91:9)

Sources & evidence

ORD record
ord-1f72710c282245aab25ab67265500023
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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