Hydrochloric Acid → Hydrochloric Acid

HRID 1037432Notes

Reaction equation

HRID 1037432 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([CH:12]=[CH2:13])[N:8]=[CH:9][CH:10]=2)[O:5][C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][CH2:27]2)=[CH:22][CH:21]=1.[ClH:38].O1CCOCC1>C(Cl)Cl>[NH2:30][C:26]1([C:23]2[CH:22]=[CH:21][C:20]([C:3]3[C:2](=[O:1])[C:11]4[C:6]([O:5][C:4]=3[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:7]([CH2:12][CH2:13][Cl:38])[N:8]=[CH:9][CH:10]=4)=[CH:25][CH:24]=2)[CH2:27][CH2:28][CH2:29]1.[ClH:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67067944HCID 67067944, compound

Product 2

HCID 313Hydrochloric AcidYield 38%HCID 67068011HCID 67068011, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-(4-(4-oxo-2-phenyl-8-vinyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate (15 mg, 0.030 mmol) in DCM was added 4 M HCl in 1,4-dioxane (0.05 mL, 2 mmol). The reaction mixture was stirred at RT for 4 h. The solvents were removed in vacuo. The product was chromatographed on a 5 g C18 cartridge {gradient 10 to 50% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as an HCl salt (5 mg, 38%). 1H NMR (500 MHz, CD3OD): δ 8.61 (d, 1H), 7.95 (d, 1H), 7.51-7.30 (m, 9H), 4.15-4.08 (m, 2H), 3.68-3.60 (m, 2H), 2.75-2.67 (m, 2H), 2.55-2.42 (m, 2H), 2.28-2.12 (m, 1H), 1.98-1.88 (m, 1H). LCMS (Method I): RT=4.49 min, [M+2]+=432.

Workup

  1. customThe solvents were removed in vacuo
  2. customThe product was chromatographed on a 5 g C18 cartridge {gradient 10 to 50% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)}

Sources & evidence

ORD record
ord-0f70034b8efb408788e454738f980572
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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