Diisopropylethylamine → HCID 178502300, compound

HRID 2203126Notes

Reaction equation

HRID 2203126 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]([CH:18]4[CH2:20][CH2:19]4)[CH2:15][NH:14]3)[NH:11][CH:12]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:30][O:31][C:32]([NH:34][C@@H:35]([CH:39]([CH3:41])[CH3:40])[C:36](O)=[O:37])=[O:33].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH3:30][O:31][C:32](=[O:33])[NH:34][C@H:35]([C:36]([N:14]1[CH2:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[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:37])[CH:39]([CH3:41])[CH3:40]

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 178419349HCID 178419349, compound

Product 1

HCID 178502300HCID 178502300, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-bromo-phenyl)-2-((S)-4-cyclopropyl-2,5-dihydro-1H-pyrrol-2-yl)-1H-imidazole (1.8 g, 5.45 mmol) in DCM (30 mL) was added DIPEA (3.52 g, 27.25 mmol), (S)-2-methoxycarbonylamino-3-methyl-butyric acid (1.14 g, 6.54 mmol) and HATU (2.49 g, 6.54 mmol). The mixture was stirred at RT overnight washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated. The resulting material was combined with the product of a separate batch prepared at the 0.61 mmol scale by the same process and purified by column chromatography (20%-50% EtOAc in petroleum ether) to give the desired product, which was purified by SFC separation to give the title intermediate (800 mg, 30% yield). m/z): [M+H]+ calcd for C23H27BrN4O3 487.13, 489.12 found 487.1.

Workup

  1. washwashed with water (50 mL) and brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customprepared at the 0.61 mmol scale by the same process
  6. custompurified by column chromatography (20%-50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-590ef763baa94991bff62d0112334865
Source dataset
uspto-grants-2016_06
Patent number
US09365549B2

Reaction notes

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