1,4-Dihydro-2,6-dimethyl-4-(3-isothiocyanatophenyl)-3,5-pyrazinedicarboxylic acid, dimethyl ester → HCID 178498419, compound

HRID 566904Notes

Reaction equation

HRID 566904 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:25])=[C:5]([C:21]([O:23][CH3:24])=[O:22])[N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N:18]=[C:19]=S)[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[N:26]#[C:27][NH2:28].[Na].[C:30]1([CH:36]2[CH2:41][CH2:40][N:39]([CH2:42][CH2:43][CH2:44][NH2:45])[CH2:38][CH2:37]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CCO.C1COCC1.Cl[Hg]Cl>[C:27]([N:28]=[C:19]([NH:18][C:14]1[CH:13]=[C:12]([N:6]2[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:2]([CH3:1])[NH:3][C:4]([CH3:25])=[C:5]2[C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:16][CH:15]=1)[NH:45][CH2:44][CH2:43][CH2:42][N:39]1[CH2:38][CH2:37][CH:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:41][CH2:40]1)#[N:26]

Participants

7

Reactant 3

HCID 155242381,4-Dihydro-2,6-dimethyl-4-(3-isothiocyanatophenyl)-3,5-pyrazinedicarboxylic acid, dimethyl esterHCID 22725156HCID 22725156, compoundHCID 57375518Cyanamidnatrium

Product 1

HCID 178498419HCID 178498419, compound

Reagents, catalysts & solvents 3

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1,4-Dihydro-2,6-dimethyl-4-(3-isothiocyanatophenyl)-3,5-pyrazinedicarboxylic acid, dimethyl ester (144 mg, 0.40 mmol) was added into sodium cyanamide (28 mg, 0.44 mmol) in 3 mL of EtOH and the mixture was stirred for 20 minutes. EtOH was then removed in vacuo and the resultant foam-like material was mixed with 4-phenyl-piperidine-1-propanamine (105 mg, 0.48 mmol) in 5 mL of THF. The mixture was cooled down to 0° C. and HgCl2 (109 mg) was added. The reaction was completed in 15 min. After filtration and extraction, the organic layer was concentrated and purified by chromatography (silica gel, eluted with 10% (v/v) methanol in methylene chloride) to yield the title compound as isolated as a yellow foam (175 mg, 75%); 1H-NMR (CDCl3) δ 7.05-7.35 (m, 6H), 6.75 (br, 1H), 6.65 (d, 1H, J=7.5 Hz), 6.58 (d, 1H, J=8.3 Hz), 6.53 (br, 1H), 5.98 (br, 1H), 3.72 (s, 6H), 3.38 (m, 2H), 2.97 (m, 2H), 2.30-2.55 (m, 3H), 2.39 (s, 6H), 2.03 (m, 2H), 1.65-1.80 (m, 4H), 1.40-1.60 (m, 2H); 13C-NMR (CDCl3) δ 166.2, 152.6, 149.4, 129.9, 128.5, 126.9, 126.3, 118.3, 116.3, 112.5, 110.4, 108.7, 54.1, 51.8, 42.4, 41.0, 32.7, 29.8, 25.6, and 17.9.

Workup

  1. customEtOH was then removed in vacuo
  2. waitThe reaction was completed in 15 min
  3. filtrationAfter filtration and extraction
  4. concentrationthe organic layer was concentrated
  5. custompurified by chromatography (silica gel, eluted with 10% (v/v) methanol in methylene chloride)

Sources & evidence

ORD record
ord-cb6c1ecab6774aa2844db12bb35b7db2
Source dataset
uspto-grants-2001_01
Patent number
US06177429B1

Reaction notes

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