Triethylamine → HCID 178495074, compound

HRID 579013Notes

Reaction equation

HRID 579013 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].[CH3:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][NH2:31].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.[Cl-].[NH4+]>CN(C=O)C>[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]([NH:31][CH2:30][CH2:29][CH2:28][CH2:27][O:26][CH3:25])=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[C:5]([CH3:24])[CH:4]=1)#[N:2]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 5339094-Methoxybutan-1-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178426451HCID 178426451, compound

Product 1

HCID 178495074HCID 178495074, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Combined 6-(4-(4-cyano-2-methylphenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (50 mg, 0.156 mmol) and 4-methoxybutan-1-amine (29.0 mg, 0.281 mmol) in DMF (1 mL). Then added a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (50 mg, 0.261 mmol) and triethylamine (0.121 mL, 0.868 mmol) in DMF (0.5 mL), and a solution of HOBT (35 mg, 0.259 mmol) in DMF (0.5 mL). The mixture was then stirred overnight at room temperature. Into the reaction mixture was then poured 20 mL of saturated ammonium chloride solution and was rigorously stirred for 1 hour to give a solid. The solid was collected on by filtration, washed three times with saturated ammonium chloride solution, and then twice with ether, before being dried to give the title compound (49 mg, 77% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50-1.61 (m, 4 H) 2.42 (s, 3 H) 3.23 (s, 3 H) 3.25-3.45 (m, 8 H) 7.42-7.47 (m, 1 H) 7.49 (s, 1 H) 7.80 (s, 1 H) 8.19 (dd, J=8.72, 2.40 Hz, 1 H) 8.27 (d, J=8.34 Hz, 1 H) 8.49-8.57 (m, 2 H) 8.83 (d, J=2.02 Hz, 1 H). MS m/z [M+H]+ 406.2.

Workup

  1. stirringwas rigorously stirred for 1 hour
  2. customto give a solid
  3. filtrationThe solid was collected on by filtration
  4. washwashed three times with saturated ammonium chloride solution
  5. dry with materialtwice with ether, before being dried

Sources & evidence

ORD record
ord-6ca195819bdb4e3b8a4174f19ed7323f
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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