Hydrochloric Acid → HCID 89650662, compound

HRID 2174245Notes

Reaction equation

HRID 2174245 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[C:9]([NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:10].[NH2:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1.Cl>CCO>[Cl:8][C:6]1[CH:7]=[C:2]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:28][CH:29]=2)[C:3]([C:9](=[O:10])[NH:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2337Benzocaine2×HCID 89650598HCID 89650598, compound

Product 1

HCID 89650662HCID 89650662, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 4,6-dichloro-N-(3-pyridyl)pyridine-3-carboxamide (500 mg, 1.9 mmol) in EtOH (5 mL) was added ethyl 4-aminobenzoate (340 mg, 2.1 mmol) and HCl (0.1 mL, 4M). The mixture was heated in a microwave for 10 min at 100° C. then heated again at 130° C. for 20 min. More ethyl 4-aminobenzoate (100 mg, 0.6 mmol) was added and the mixture heated again at 130° C. for 20 min. The mixture was evaporated to dryness and the residue purified by flash chromatography (40 g Reveleris silica cartridge, 0-10% MeOH in DCM) to afford ii as an off white solid (334 mg, 46%). A 10 mg sample of ii was dissolved in DMSO and purified further using reverse phase preparatory HPLC (20-60% MeCN in water, 0.1% formic acid) to afford 8.74 mg of ii as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.85 (d, J=2.2 Hz, 1H), 8.65 (s, 1H), 8.33 (d, J=3.7 Hz, 1H), 8.11 (ddd, J=8.3, 2.5, 1.5 Hz, 1H), 7.96 (d, J=8.6 Hz, 2H), 7.40 (dd, J=8.1, 4.4 Hz, 3H), 7.15 (s, 1H), 4.30 (q, J=7.1 Hz, 2H), 1.32 (t, J=7.1 Hz, 31-1). [M+H]+ m/z=397.09.

Workup

  1. temperaturethen heated again at 130° C. for 20 min
  2. temperaturethe mixture heated again at 130° C. for 20 min
  3. customThe mixture was evaporated to dryness
  4. customthe residue purified by flash chromatography (40 g Reveleris silica cartridge, 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-d804c243f2f1418a9fcb292fca124ba8
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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