Hydrochloric Acid → HCID 47370290, compound

HRID 416234Notes

Reaction equation

Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[NH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.Cl.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>C1COCC1.CN(C=O)C>[CH3:18][O:17][C:15](=[O:16])[C:14]1[CH:19]=[CH:20][C:11]([CH2:10][NH:9][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A stirred suspension of 2,6-dichloropyrazine (500 mg, 3.36 mmol), methyl 4-(aminomethyl)benzoate.HCl (744 mg, 3.69 mmol) and i-Pr2NEt (2.05 mL, 11.75 mmol) in a mixture of anhydrous THF/DMF (10 mL/2 mL) under nitrogen was heated at 90° C. for 24 h. The mixture was allowed to cool down to room temperature, was poured into saturated aqueous NH4Cl and extracted with AcOEt. The organic layer was washed with H2O and brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (AcOEt/CH2Cl2: 20/80→30/70) to afford the title compound 62 (300 mg, 1.08 mmol, 32% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.18 (t, J=6.0 Hz, 1H), 7.97 (s, 1H), AB system (δA=7.95, δB=7.49, JAB=8.5 Hz, 4H), 7.75 (s, 1H), 4.58 (d, J=5.9 Hz, 2H), 3.87 (s, 3H).

Workup

temperatureto cool down to room temperature
extractionextracted with AcOEt
washThe organic layer was washed with H2O and brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography on silica gel (AcOEt/CH2Cl2: 20/80→30/70)

Sources & evidence

ORD record: ord-e1e99e7babe04277925f21ce24ce676e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088805B2

Reaction notes

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