Lithium Chloride → HCID 178495301, compound

HRID 526542Notes

Reaction equation

HRID 526542 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][N:13]([C:17]3[CH:30]=[CH:29][C:20]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])=[O:22])=[CH:19][N:18]=3)[C:14]=2[O:15]C)=[CH:6][C:5]=1[F:31])#[N:2].[Cl-].[Li+]>CC(N(C)C)=O.CS(C)=O>[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][N:13]([C:17]3[CH:30]=[CH:29][C:20]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])=[O:22])=[CH:19][N:18]=3)[C:14]=2[OH:15])=[CH:6][C:5]=1[F:31])#[N:2]

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 1176013806-(4-(4-(cyanomethyl)-3-fluorophenyl)-5-methoxy-1H-pyrazol-1-yl)-N-(3-methoxypropyl)nicotinamide

Product 1

HCID 178495301HCID 178495301, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 31374DimethylacetamideSolvent

Procedure

Combined 6-(4-(4-(cyanomethyl)-3-fluorophenyl)-5-methoxy-1H-pyrazol-1-yl)-N-(3-methoxypropyl)nicotinamide (27 mg, 0.064 mmol) and lithium chloride (27.0 mg, 0.638 mmol) in DMA (1.0 mL) and heated at 60° C. for 24 h. The reaction mixture was diluted with 0.2 mL DMSO and purified by prep HPLC (formic acid conditions) to give the title compound (15 mg, 57.5% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.79 (quin, J=6.7 Hz, 2H) 3.25 (s, 3H) 3.30-3.37 (m, 2H) 3.40 (t, J=6.3 Hz, 2H) 4.03 (s, 2H) 7.42 (br. s., 1H) 7.52-8.06 (m, 2H) 8.41 (br. s., 1H) 8.50-8.82 (m, 3H) 8.91 (d, J=1.5 Hz, 1H) 13.28 (br. s., 1H). MS m/z 410 [M+H]+.

Workup

  1. custompurified by prep HPLC (formic acid conditions)

Sources & evidence

ORD record
ord-41557cf9cfb34c70a9df5a0937ad8770
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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