Hydrochloric Acid → HCID 178492256, compound

HRID 526436Notes

Reaction equation

HRID 526436 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[CH:15]N(C)C)[C:10](OCC)=[O:11])=[C:5]([O:19][CH3:20])[CH:4]=1)#[N:2].[NH:21]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][N:24]=1)[NH2:22].Cl.CCN(C(C)C)C(C)C>CC(O)C.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:15]=[N:22][N:21]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][N:24]=3)[C:10]=2[OH:11])=[C:5]([O:19][CH3:20])[CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 81531DiisopropylethylamineHCID 37826176-Hydrazinonicotinic acidHCID 117601030Ethyl 2-(4-cyano-2-methoxyphenyl)-3-(dimethylamino)acrylate

Product 1

HCID 178492256HCID 178492256, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Combined ethyl 2-(4-cyano-2-methoxyphenyl)-3-(dimethylamino)acrylate (1.427 g, 5.20 mmol), 6-hydrazinylnicotinic acid (0.664 g, 4.34 mmol), and HCl (4.34 mL, 4.34 mmol) in 2-propanol (21.7 mL) and stirred at room temperature for 8 hours to give a solid. The solid was collected by filtration and combined with Hunig's base (1.50 mL, 8.61 mmol) in 2-propanol (10 mL) and water (1 mL) and stirred for 32 hours at 50° C., then 10 mL of 1 N HCl was added and the reaction was filtered to give a solid. The solid was washed with 30 mL MeOH and 30 mL of ether and dried in vacuo to give the title compound (708 mg, 73.3%) as a beige solid. MS m/z [M+H]+ 337.3.

Workup

  1. customto give a solid
  2. filtrationThe solid was collected by filtration
  3. filtrationthe reaction was filtered
  4. customto give a solid
  5. washThe solid was washed with 30 mL MeOH and 30 mL of ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-520e36317e954ff09ae2c7bc352b1f2c
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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