Diisopropylethylamine → HCID 68156410, compound

HRID 1892732Notes

Reaction equation

HRID 1892732 reaction equation
[CH3:1][CH:2]([CH3:30])[CH2:3][CH:4]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][N:22]=1)[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[N:12]2)=[CH:7][CH:6]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:56][CH2:57][CH2:58][C:59]([O:61][CH3:62])=[O:60].C(N(C(C)C)CC)(C)C>CN(C)C=O.[Cl-].[NH4+]>[CH3:30][CH:2]([CH3:1])[CH2:3][CH:4]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:56][CH2:57][CH2:58][C:59]([O:61][CH3:62])=[O:60])=[O:27])=[CH:23][N:22]=1)[C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH:15]=[C:14]([C:16]([F:18])([F:17])[F:19])[CH:13]=[N:12]2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68156265HCID 68156265, compound

Product 1

HCID 68156410HCID 68156410, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of (+/−)-6-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)butylamino)nicotinic acid (50 mg, 0.12 mmol) in N,N-dimethylformamide (5 mL) was added 0-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (67.7 mg, 0.178 mmol). The mixture was stirred for 45 minutes. Methyl 3-aminopropionate hydrochloride (24.6 mg, 0.178 mmol) and diisopropylethylamine (61.5 mg, 0.476 mmol) were added. The resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with saturated ammonium chloride. The solution was extracted three times with ethyl acetate. The combined organics were washed with water, dried over sodium sulfate, filtered and concentrated to give methyl 3-(6-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)butylamino)nicotinamido)propanoate (50 mg, 83%) as a brown oil. MS (M+1): 504.1.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. extractionThe solution was extracted three times with ethyl acetate
  3. washThe combined organics were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-47c13a110036412d9c18f91023caf4b2
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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