Hydrochloric Acid → 3-(4-(1-aminocyclobutyl)phenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridine-8-carbonitrile hydrochloride

HRID 1037430Notes

Reaction equation

HRID 1037430 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[C:12](=[O:13])[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4([NH:24]C(=O)OC(C)(C)C)[CH2:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)=[C:10]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:9][C:8]=12)#[N:2].[ClH:38]>C(Cl)Cl.O1CCOCC1>[ClH:38].[NH2:24][C:20]1([C:17]2[CH:16]=[CH:15][C:14]([C:11]3[C:12](=[O:13])[C:7]4[C:8]([O:9][C:10]=3[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[C:3]([C:1]#[N:2])[N:4]=[CH:5][CH:6]=4)=[CH:19][CH:18]=2)[CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68227519tert-butyl 1-(4-(8-cyano-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

Product 1

HCID 670678703-(4-(1-aminocyclobutyl)phenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridine-8-carbonitrile hydrochlorideYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 1-(4-(8-cyano-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate (10 mg, 0.020 mmol) in DCM (2 mL) was added 4M HCl in 1,4-dioxane (1.0 ml). The reaction mixture was stirred at RT for overnight. The solvent was evaporated and the crude product was washed several times with DCM and acetonitrile (3×1 ml). The product was dried to give the title compound as the HCl salt (5 mg, 71%). 1H NMR (500 MHz, CD3OD): δ 8.55 (d, 1H), 8.15 (d, 1H), 7.48-7.18 (m, 9H), 2.75-2.67 (m, 2H), 2.55-2.42 (m, 2H), 2.18-2.09 (m, 1H), 1.88-1.73 (m, 1H). LCMS (Method I): RT=4.39 min, [M+2]+=395.

Workup

  1. customThe solvent was evaporated
  2. washthe crude product was washed several times with DCM and acetonitrile (3×1 ml)
  3. customThe product was dried

Sources & evidence

ORD record
ord-c562e43e16084cb58d33f0cfb9ec5734
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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