Hydrochloric Acid → HCID 178502472, compound

HRID 1751344Notes

Reaction equation

HRID 1751344 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:26](=[CH:27][CH:28]=1)[C:8]1[NH:9][C:10]([C@@H:12]3[C@@H:17]4[CH2:18][C@@H:14]([CH2:15][CH2:16]4)[N:13]3C(OC(C)(C)C)=O)=[N:11][C:7]=1[CH:6]=[CH:5]2.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.CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:26](=[CH:27][CH:28]=1)[C:8]1[NH:9][C:10]([C@@H:12]3[C@@H:17]4[CH2:18][C@@H:14]([CH2:15][CH2:16]4)[N:13]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:11][C:7]=1[CH:6]=[CH:5]2

Participants

9

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 178452509HCID 178452509, compound

Product 1

HCID 178502472HCID 178502472, compoundYield 54.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(1R,3S,4S)-tert-butyl 3-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (200 mg, 0.45 mmol) in DCM (5 mL) was added HCl (4M in dioxane, 1 mL). The solution stirred for 1 h, after which the solvent was removed. The intermediate (154 mg, 0.45 mmol) was dissolved in DMF (5 mL). (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (79 mg, 0.45 mmol), HATU (171 mg, 0.45 mmol), and DIPEA (0.39 mL, 2.25 mmol) were added sequentially. After stirring o/n, the solution was diluted with EtOAc, washed with sat. NaHCO3, brine, dried with MgSO4, and concentrated. The mixture was purified by silica gel chromatography to yield product (122 mg).

Workup

  1. customafter which the solvent was removed
  2. stirringAfter stirring o/n, the solution
  3. washwashed with sat. NaHCO3, brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7bd5e9081c9f45acada43dccb2f20bc0
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

Loading…