Hydrochloric Acid → HCID 178487655, compound

HRID 526397Notes

Reaction equation

HRID 526397 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].CN(C)[CH:14]=[C:15]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[CH:22]=1)[C:16](OCC)=[O:17].Cl.CCN(C(C)C)C(C)C>CC(O)C>[OH:17][C:16]1[N:1]([C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]=2)[N:2]=[CH:14][C:15]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 37826176-Hydrazinonicotinic acidHCID 131732874Ethyl 3-(dimethylamino)-2-(2-methoxypyridin-4-yl)acrylate

Product 1

HCID 178487655HCID 178487655, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combined 6-hydrazinylnicotinic acid (167 mg, 1.090 mmol), ethyl 3-(dimethylamino)-2-(2-methoxypyridin-4-yl)acrylate (300 mg, 1.199 mmol), 2-propanol (3632 μl), and hydrochloric acid (1.85% aqueous, 2.15 mL, 1.090 mmol). The reaction was stirred at room temperature. After 1 hour Hunig's base (949 μl, 5.45 mmol) was added to the suspension which became a yellow solution. The reaction was washed with EtOAc (2×15 mL) and the aqueous phase was concentrated in vacuo, yielding a yellow solid. The solid was triturated with 1N HCl (50 mL), collected by filtration, and washed with water. The solid was then slurried in methanol (2×60 mL) and diethyl ether (2×60 mL), the dried under vacuum to give the title compound. MS m/z [M+H]+ 313.0.

Workup

  1. washThe reaction was washed with EtOAc (2×15 mL)
  2. concentrationthe aqueous phase was concentrated in vacuo
  3. customyielding a yellow solid
  4. customThe solid was triturated with 1N HCl (50 mL)
  5. filtrationcollected by filtration
  6. washwashed with water
  7. dry with materialdiethyl ether (2×60 mL), the dried under vacuum

Sources & evidence

ORD record
ord-caa518c66e0241b2a9a3b22bfbb1f1fc
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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