Diisopropylethylamine → HCID 178502304, compound

HRID 2203125Notes

Reaction equation

HRID 2203125 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C@@H:13]3[CH:17]=[C:16]([CH3:18])[CH2:15][NH:14]3)[NH:11][CH:12]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:28][O:29][C:30]([NH:32][C@@H:33]([CH:37]([CH3:39])[CH3:38])[C:34](O)=[O:35])=[O:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:28][O:29][C:30](=[O:31])[NH:32][C@H:33]([C:34]([N:14]1[CH2:15][C:16]([CH3:18])=[CH:17][C@H:13]1[C:10]1[NH:11][CH:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[N:9]=1)=[O:35])[CH:37]([CH3:39])[CH3:38]

Participants

6

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 178427882HCID 178427882, compound

Product 1

HCID 178502304HCID 178502304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-bromo-phenyl)-2-((S)-4-methyl-2,5-dihydro-1H-pyrrol-2-yl)-1H-imidazole (1.10 g, 3.62 mmol) in DCM (50 mL) was added DIPEA (2.34 g, 18.1 mmol), (S)-2-methoxycarbonylamino-3-methyl-butyric acid (761 mg, 4.34 mmol) and HATU (1.65 g, 4.34 mmol). The mixture was stirred at RT overnight, washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered, concentrated and purified by column chromatography (10%-50% EtOAc in petroleum ether) to give the desired product, which was purified by supercritical fluid chromatography (SFC) [mobile phase A: supercritical CO2, phase B: methanol+0.05% diethylamine; flow rate: 80 mL/min] to give the title intermediate (750 mg, 45% yield). m/z): [M+H]+ calcd for C21H25BrN4O3 461.11, 463.11 found 461.1.

Workup

  1. washwashed with water (50 mL) and brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography (10%-50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-7dc38f2613724aa4afced36f6f163b4f
Source dataset
uspto-grants-2016_06
Patent number
US09365549B2

Reaction notes

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