Hydrochloric Acid → HCID 178509615, compound

HRID 526400Notes

Reaction equation

HRID 526400 reaction equation
[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=1)[NH2:2].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20](=[CH:26]N(C)C)[C:21](OCC)=[O:22])=[CH:16][CH:15]=1)#[N:13].Cl.CCN(C(C)C)C(C)C>CC(O)C>[C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:26]=[N:2][N:1]([C:3]3[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=3)[C:21]=2[OH:22])=[CH:16][CH:15]=1)#[N:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 37826176-Hydrazinonicotinic acidHCID 117601544Ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate

Product 1

HCID 178509615HCID 178509615, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combined 6-hydrazinylnicotinic acid (6.00 g, 39.2 mmol) and ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate (10.05 g, 41.1 mmol) and 2-propanol (80 mL) and treated with 1.85% hydrochloric acid (77 mL, 39.2 mmol). The reaction was stirred at room temperature for 16 h, then Hunig's base (34.1 mL, 196 mmol) was add to the suspension which became homogeneous. The mixture was stirred for 3 h. The reaction mixture was washed with isopropyl acetate (2×150 mL). The combined organic layers were extracted with water (40 mL) and the combined aqueous layers were concentrated in vacuo to give a solid. The solid was triturated with 1N HCl (300 mL), filtered and washed with water (20 mL), then slurried in ethanol (350 mL) and granulated overnight. The solid was collected by filtration and dried in vacuum to give the title compound (9.20 g, 77% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.79 (d, J=8.34 Hz, 2H) 8.14 (br. s., 2H) 8.47 (d, J=7.07 Hz, 1H) 8.71 (br. s., 2H) 8.97 (s, 1H) 13.44 (br. s., 1H) 13.60 (br. s., 1H). MS [M+H]307.

Workup

  1. stirringThe mixture was stirred for 3 h
  2. washThe reaction mixture was washed with isopropyl acetate (2×150 mL)
  3. extractionThe combined organic layers were extracted with water (40 mL)
  4. concentrationthe combined aqueous layers were concentrated in vacuo
  5. customto give a solid
  6. customThe solid was triturated with 1N HCl (300 mL)
  7. filtrationfiltered
  8. washwashed with water (20 mL)
  9. waitslurried in ethanol (350 mL) and granulated overnight
  10. filtrationThe solid was collected by filtration
  11. customdried in vacuum

Sources & evidence

ORD record
ord-e26f3241a5404f938c8c11f6afc299c8
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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