Triethylamine → HCID 178426435, compound

HRID 526581Notes

Reaction equation

HRID 526581 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](O)=[O:20])=[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.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[CH3:55][NH:56][CH2:57][CH2:58][CH2:59][N:60]1[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]1>CN(C=O)C.CS(C)=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:56]([CH3:55])[CH2:57][CH2:58][CH2:59][N:60]4[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]4)=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 409699Methyl-(3-piperidin-1-yl-propyl)-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178426451HCID 178426451, compound

Product 1

HCID 178426435HCID 178426435, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

Combined 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (70 mg, 0.219 mmol), HOBT hydrate (50.2 mg, 0.328 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (62.8 mg, 0.328 mmol) in DMF (1 mL), and added triethylamine (0.092 mL, 0.656 mmol), then stirred at ambient temperature for 5 minutes and N-methyl-3-(piperidin-1-yl)propan-1-amine (0.085 mL, 0.437 mmol) was added. The reaction was stirred at 50° C. for 3 hours. The crude reaction was then cooled to ambient temperature and diluted with DMSO (1 mL) and purified via preparative HPLC (25-45% acetonitrile in water, with trifluoroacetic acid) to give the title compound (61.5 mg, 0.134 mmol, 61.4%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30-1.49 (m, 1H) 1.68 (br. s., 3H) 1.82 (br. s., 2H) 1.93-2.07 (m, 2H) 2.43 (s, 3H) 2.88-3.15 (m, 7H) 3.31-3.43 (m, 1H) 3.45-3.58 (m, 3H) 7.65-7.87 (m, 3H) 8.04-8.67 (m, 4H) 9.35 (br. s., 1H). ESI-MS m/z [M+H]+ 459.3.

Workup

  1. stirringThe reaction was stirred at 50° C. for 3 hours
  2. customThe crude reaction
  3. temperaturewas then cooled to ambient temperature
  4. custompurified via preparative HPLC (25-45% acetonitrile in water, with trifluoroacetic acid)

Sources & evidence

ORD record
ord-f0322ba7aec543a9bdd578b1f457771b
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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