Diisopropylethylamine → HCID 86682791, compound

HRID 1500516Notes

Reaction equation

HRID 1500516 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:10]([CH3:12])[CH3:11])[C:7](O)=[O:8])=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.[Br:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[NH:50][C:49]([C@@H:51]3[CH2:55][C@H:54]([CH3:56])[CH2:53][NH:52]3)=[N:48][CH:47]=2)=[CH:42][CH:41]=1.C(N(CC)C(C)C)(C)C>CC(N(C)C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@H:6]([C:7]([N:52]1[CH2:53][C@@H:54]([CH3:56])[CH2:55][C@H:51]1[C:49]1[NH:50][C:46]([C:43]2[CH:44]=[CH:45][C:40]([Br:39])=[CH:41][CH:42]=2)=[CH:47][N:48]=1)=[O:8])[CH:10]([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 131734276HCID 131734276, compound

Product 1

HCID 86682791HCID 86682791, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of (S)-2-methoxycarbonylamino-3-methyl-butyric acid (103 mg, 0.59 mmol, Preparation 2) and HATU (270 mg, 0.71 mmol) were stirred in DMA (2 mL) for 10 min and then 5-(4-bromo-phenyl)-2-((2S,4S)-4-methyl-pyrrolidin-2-yl)-1H-imidazole 2 HCl (224 mg, 0.59 mmol, Preparation 8) and N,N-diisopropylethylamine (0.31 mL, 1.8 mmol) were added. The resulting mixture was stirred at RT overnight, diluted with ethyl acetate (50 mL), and washed with water (2×5 mL). The organic layer was dried over magnesium sulfate, filtered, concentrated and purified by silica gel chromatography (0-100% EtOAc/hexanes)). Fractions with desired product were combined and concentrated to give the title compound (183 mg, 66% yield) (m/z): [M+H]+ calcd for C21H27BrN4O3 463.13, 465.12 found 465.3.

Workup

  1. washwashed with water (2×5 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-100% EtOAc/hexanes))
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b551ab9d55e242408c69460358fb0a0c
Source dataset
uspto-grants-2015_12
Patent number
US09206159B2

Reaction notes

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