Acetylcysteamine → 7-(2-acetamidoethylthio)-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79481

Reaction equation

F[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH2:31][CH3:32])=[N:17][N:18]4[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[SH:33][CH2:34][CH2:35][NH:36][C:37](=[O:39])[CH3:38].CC(C)([O-])C.[K+]>O1CCOCC1>[C:37]([NH:36][CH2:35][CH2:34][S:33][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH2:31][CH3:32])=[N:17][N:18]4[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1)(=[O:39])[CH3:38]

Participants

Conditions

Temperature: 95 °C

Procedure

N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide (0.028 g, 0.065 mmol) (Example 74, Step A), N-(2-mercaptoethyl)acetamide (0.078 g, 0.65 mmol), and potassium tert-butoxide (0.022 g, 0.20 mmol) were added to a minimal amount of deoxygenated 1,4-dioxane in a sealed tube and heated for 18 hours at 95° C. The reaction mixture was cooled, concentrated under reduced pressure and purified by silica gel chromatography eluting with methanol (containing 6% ammonium hydroxide) and dichloromethane (1:9), to yield the product (20 mg) as a white powder. MS ESI (+) m/z 528 (M+1) detected.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
custompurified by silica gel chromatography
washeluting with methanol (containing 6% ammonium hydroxide) and dichloromethane (1:9)

Sources & evidence

ORD record: ord-667f07dc02a9466c8e3966d61737eb20
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841455B2

Linked notes

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