Hydrochloric Acid → HCID 67681543, compound

HRID 1751336Notes

Reaction equation

HRID 1751336 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]3C(OC(C)(C)C)=O)=[N:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[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.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]3[C:36](=[O:37])[C@@H:35]([NH:34][C:32](=[O:33])[O:31][CH3:30])[CH:39]([CH3:41])[CH3:40])=[N:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 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 69675358HCID 69675358, compound

Product 1

HCID 67681543HCID 67681543, compoundYield 37.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To (S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)indoline-1-carboxylate (1.41 g, 3.2 mmol) in DCM (20 mL) was added HCl (4M in dioxane, 4 mL). The solution stirred for 2 h, and the solvent was removed. The intermediate was dissolved in DMF (30 mL). (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (560 mg, 3.2 mmol), HATU (1.22 g, 3.2 mmol), and DIPEA (2.79 mL, 16 mmol) were added sequentially. The solution stirred for 3 h, diluted with EtOAc, washed with sat. NaHCO3, brine, dried over MgSO4, and concentrated. The mixture was purified by silica gel chromatography to yield product (600 mg).

Workup

  1. customthe solvent was removed
  2. dissolutionThe intermediate was dissolved in DMF (30 mL)
  3. stirringThe solution stirred for 3 h
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-66777311ea34455caf95c34a184a0f8a
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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