Acetonitrile → HCID 178495306, compound

HRID 526647Notes

Reaction equation

HRID 526647 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:16]3[CH:29]=[CH:28][C:19]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])=[O:21])=[CH:18][N:17]=3)[C:13]=2[O:14]C)=[CH:5][C:4]=1[CH3:30])#[N:2].[Cl-].[Li+].C(#N)C>CC(N(C)C)=O.CS(C)=O.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:16]3[CH:29]=[CH:28][C:19]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27])=[O:21])=[CH:18][N:17]=3)[C:13]=2[OH:14])=[CH:5][C:4]=1[CH3:30])#[N:2]

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 433294Lithium ChlorideHCID 1176013996-(4-(4-cyano-3-methylphenyl)-5-methoxy-1H-pyrazol-1-yl)-N-(3-methoxypropyl)nicotinamide

Product 1

HCID 178495306HCID 178495306, compoundYield 26.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

Combined 6-(4-(4-cyano-3-methylphenyl)-5-methoxy-1H-pyrazol-1-yl)-N-(3-methoxypropyl)nicotinamide (54.7 mg, 0.135 mmol) and lithium chloride (57.2 mg, 1.350 mmol) in DMA (2109 μl) and heated at 60° C. for 24 hours. The reaction mixture was then diluted with 0.6 mL DMSO and purified by preparative HPLC (35-60% acetonitrile in water under TFA conditions) and then again (15-40% acetonitrile in water under basic conditions) to give the title compound (14 mg, 0.036 mmol, 26.5%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.77 (quin, J=6.63 Hz, 2H) 2.43 (s, 3H) 3.25 (s, 3H) 3.38-3.41 (m, 4H) 7.08 (br. s., 2H) 7.58 (d, J=8.08 Hz, 1H) 7.88 (d, J=9.35 Hz, 1H) 7.97 (s, 1H) 8.29 (dd, J=8.46, 2.40 Hz, 1H) 8.50 (d, J=8.34 Hz, 1H) 8.61 (t, J=6.06 Hz, 1H) 8.85 (d, J=1.77 Hz, 1H); MS (M+H)+392.

Workup

  1. custompurified by preparative HPLC (35-60% acetonitrile in water under TFA conditions)

Sources & evidence

ORD record
ord-39f83c2fc6764c679abdf46ed74aeece
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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