Hydrochloric Acid → HCID 178495302, compound

HRID 579006Notes

Reaction equation

HRID 579006 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])=[CH:5][CH:4]=1)#[N:2].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.CCN(C(C)C)C(C)C.[CH3:55][O:56][CH2:57][CH2:58][CH2:59][NH2:60].Cl>CN(C=O)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]([NH:60][CH2:59][CH2:58][CH2:57][O:56][CH3:55])=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:5][CH:4]=1)#[N:2]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 16723-MethoxypropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 178509615HCID 178509615, compound

Product 1

HCID 178495302HCID 178495302, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combined 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (4.00 g, 13.06 mmol), EDCI (3.76 g, 19.59 mmol), and HOBT hydrate (3.00 g, 19.59 mmol) in DMF (39.6 mL) and treated with Hunig's base (6.82 mL, 39.2 mmol). Then 3-methoxypropan-1-amine (2.005 mL, 19.59 mmol) was added and the reaction mixture was stirred at ambient temperature for 24 h. The reaction mixture was then diluted with water (200 mL) and acidified with HCl (aq., 1N) until pH=5 and stirred to give a fine suspension. The solid was collected by filtration, suspended in MeOH (150 mL), and heated to reflux for 8 hours, the slowly cooled to ambient temperature. The solid was collected by filtration and dried in vacuum to give the title compound (4.25 g, 11.26 mmol, 86% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.78 (quin, J=6.63 Hz, 2 H) 3.30-3.37 (m, 2 H) 3.40 (t, J=6.32 Hz, 2 H) 7.79 (d, J=8.34 Hz, 2 H) 8.14 (d, J=6.57 Hz, 2 H) 8.31-8.69 (m, 3 H) 8.71 (t, J=5.31 Hz, 1 H) 8.91 (s, 1 H) 13.54 (br. s., 1 H). MS [M+H] 378.

Workup

  1. stirringstirred
  2. customto give a fine suspension
  3. filtrationThe solid was collected by filtration
  4. temperatureheated
  5. temperatureto reflux for 8 hours
  6. temperaturethe slowly cooled to ambient temperature
  7. filtrationThe solid was collected by filtration
  8. customdried in vacuum

Sources & evidence

ORD record
ord-490acf9692484973ac3b7fc22a60a9d5
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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