4,5-dimethyl-1H-pyrazol-3-amine → HCID 178496073, compound

HRID 1505003Notes

Reaction equation

HRID 1505003 reaction equation
[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][O:21][CH3:22])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:23])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:24][C:25]1[C:26]([NH2:31])=[N:27][NH:28][C:29]=1[CH3:30]>Cl.CCO>[ClH:23].[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][O:21][CH3:22])[N:14]=[CH:13][CH:12]=[C:11]2[NH:31][C:26]1[NH:27][N:28]=[C:29]([CH3:30])[C:25]=1[CH3:24])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 47370294,5-dimethyl-1H-pyrazol-3-amineHCID 90047039HCID 90047039, compound

Product 1

HCID 178496073HCID 178496073, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

6-(tert-Butylsulfonyl)-4-chloro-7-(2-methoxyethoxy)quinoline (0.461 g, 1.288 mmol), 4,5-dimethyl-1H-pyrazol-3-amine (0.175 g, 1.546 mmol), and 2 drops of aq HCl (0.161 ml, 0.322 mmol) in EtOH (3.06 ml) were heated at 80° C. overnight. The reaction was cooled to rt and the precipitate was filtered, washed with MeCN, and vacuum-dried to yield 6-(tert-butylsulfonyl)-N-(3,4-dimethyl-1H-pyrazol-5-yl)-7-(2-methoxyethoxy)quinolin-4-amine, hydrochloride (0.290 g, 0.618 mmol, 48.0% yield). m.p. 181-184° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.71 (s, 1H), 11.20 (br. s., 1H), 9.22 (br. s., 1H), 8.48 (d, J=7.07 Hz, 1H), 7.63 (s, 1H), 6.64 (d, J=7.07 Hz, 1H), 4.36 (t, J=4.29 Hz, 2H), 3.78 (t, J=4.29 Hz, 2H), 3.35 (s, 3H), 2.24 (s, 3H), 1.84 (s, 3H), 1.35 (s, 9H). MS: m/z: 433.2 [M+H]+.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with MeCN
  3. customvacuum-dried

Sources & evidence

ORD record
ord-76c24759c0074331afe58a45b73180b3
Source dataset
uspto-grants-2015_12
Patent number
US09216965B2

Reaction notes

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