HCID 61624701, compound → HCID 86691616, compound

HRID 522625Notes

Reaction equation

HRID 522625 reaction equation
[N:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=2)[N:5]=1)=[C:2]=[S:3].[CH3:17][C:18]1[CH:22]=[C:21]([CH3:23])[N:20]([CH:24]([CH3:29])[C:25]([NH:27][NH2:28])=[O:26])[N:19]=1>C(Cl)Cl>[CH3:17][C:18]1[CH:22]=[C:21]([CH3:23])[N:20]([CH:24]([CH3:29])[C:25]([NH:27][NH:28][C:2](=[S:3])[NH:1][C:4]2[CH:8]=[CH:7][N:6]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=3)[N:5]=2)=[O:26])[N:19]=1

Participants

4

Reactant 2

HCID 61624701HCID 61624701, compound2×HCID 86691617HCID 86691617, compound

Product 1

HCID 86691616HCID 86691616, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 74 2-[(3-isothiocyanato-1H-pyrazol-1-yl)methyl]-6-methylpyridine (101 mg, 0.439 mmol) was dissolved in 4 mL of DCM, and then Intermediate 102 2-(3,5-dimethyl-1H-pyrazol-1-yl)propanohydrazide (80 mg, 0.439 mmol) was added. The mixture was stirred at room temperature for 2 h. Solvent was evaporated under vacuum to give 2-[2-(3,5-dimethyl-1H-pyrazol-1-yl)propanoyl]-N-{1-[(6-methyl-2-pyridinyl)methyl]-1H-pyrazol-3-yl}hydrazinecarbothioamide (181 mg, 0.439 mmol, 100% yield) as yellow solid. [ES+MS] m/z 413 (MH+)]. Solid was dissolved in 5 mL of POCl3 and the mixture was stirred at 100° C., until no starting material was detected (1 h 30 minutes). Crude of reaction was partitioned between DCM and distilled water. Organic layer was dried over MgSO4 (anh), filtered and concentrated to give a light yellow solid. This solid was purified by HPLC preparative using X-Terra chromatography column (30 mm×150 mm), gradient 0% to 40% ACN/H2O, in neutral conditions to yield the title compound as a white solid (22 mg, 12.7%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 10.87 (br s, 1H), 7.77 (d, 1H), 7.59-7.65 (m, 1H), 7.15-7.17 (m, 1H), 6.77-6.80 (m, 1H), 6.01 (d, 1H), 5.83 (br s, 1H), 5.77 (q, 1H), 5.26 (s, 2H), 2.45 (s, 3H), 2.24 (s, 3H), 2.08 (s, 3H), 1.78 (d, 3H). [ES+MS] m/z 395 (MH+).

Workup

  1. customSolvent was evaporated under vacuum

Sources & evidence

ORD record
ord-0391f750d9fd424bbe7db860537229a3
Source dataset
uspto-grants-2016_05
Patent number
US09334265B2

Reaction notes

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