Hydrochloric Acid → HCID 178422218, compound

HRID 526455Notes

Reaction equation

HRID 526455 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:25]N(C)C)[C:21](OC)=[O:22])=[C:16]([CH3:29])[C:15]=1[F:30])#[N:13].Cl.C(N(C(C)C)C(C)C)C>O.CC(O)C>[C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[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])=[C:16]([CH3:29])[C:15]=1[F:30])#[N:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 37826176-Hydrazinonicotinic acidHCID 117600405Methyl 2-(4-cyano-3-fluoro-2-methylphenyl)-3-(dimethylamino)acrylate

Product 1

HCID 178422218HCID 178422218, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Combined 6-hydrazinylnicotinic acid (1.10 g, 7.18 mmol), methyl 2-(4-cyano-3-fluoro-2-methylphenyl)-3-(dimethylamino)acrylate (2.072 g, 7.90 mmol), 2-propanol (18 mL), and 0.5M aqueous hydrochloric acid (17.24 mL, 8.62 mmol). After 2 hours, N-ethyl-N-isopropylpropan-2-amine (6.26 mL, 35.9 mmol) was added. After another hour the reaction mixture was diluted with water and washed twice with IPAc. The aqueous phase was acidified to ˜pH=3.5 and stirred for 30 minutes to give a solid which was collected by filtration, washed with water, ethanol, and heptanes, and dried overnight under vacuum to give the title compound (1.60 g, 66%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (d, J=2.27 Hz, 3H) 7.64 (d, J=8.08 Hz, 1H) 7.69-7.80 (m, 1H) 8.26 (br. s., 1H) 8.48 (br. s., 2H) 8.98 (t, J=1.52 Hz, 1H) 13.45 (br. s., 2H). ESI-MS m/z [M+H]+ 339.2.

Workup

  1. washwashed twice with IPAc
  2. customto give a solid which
  3. filtrationwas collected by filtration
  4. washwashed with water, ethanol, and heptanes
  5. customdried overnight under vacuum

Sources & evidence

ORD record
ord-d1abb723487d4b8dab9bacebebb10177
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

Loading…