Hydrochloric Acid → HCID 178426438, compound

HRID 526580Notes

Reaction equation

HRID 526580 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2].C1C=C2N=NN(O)C2=CC=1.O.Cl.[CH2:37]([N:39]=[C:40]=NCCCN(C)C)C.C(N(CC)CC)C.Cl.CNC.Cl>CN(C=O)C.CO.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([N:39]([CH3:40])[CH3:37])=[O:21])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178426451HCID 178426451, compound

Product 1

HCID 178426438HCID 178426438, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combined 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (107 mg, 0.334 mmol), HOBT hydrate (77 mg, 0.501 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (96 mg, 0.501 mmol) in DMF (2 mL), and added triethylamine (0.188 mL, 1.336 mmol), stirred at ambient temperature for 5 minutes and dimethylamine hydrochloride (54.5 mg, 0.668 mmol) was added. The reaction was stirred at 50° C. for 3 hours, then cooled to ambient temperature and diluted with MeOH (5 mL), water (5 mL), and acidified to pH 5 using 1N aqueous hydrochloric acid, to give a solid which was filtered, washed with water, and dried under vacuum to give the title compound (76.2 mg, 0.219 mmol, 66%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.43 (s, 3H) 3.01 (br. s., 6H) 7.65 (dd, J=8.08, 1.52 Hz, 1H) 7.70-7.82 (m, 2H) 8.02-8.20 (m, 2H) 8.37 (br. s., 1H) 8.56 (dd, J=2.27, 0.76 Hz, 1H) 13.11 (br. s., 1H). ESI-MS m/z [M+H]+ 348.3.

Workup

  1. stirringThe reaction was stirred at 50° C. for 3 hours
  2. temperaturecooled to ambient temperature
  3. customto give a solid which
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-86fe1ca56f1c43fab3dcd9a9c1ac7ad8
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

Loading…