Hydrochloric Acid → HCID 178466743, compound

HRID 707313Notes

Reaction equation

[CH3:1][C:2]1([CH3:29])[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C@H:11]2[CH2:14][C@H:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4([CH3:27])OCC[O:23]4)=[CH:18][N:17]=3)[CH2:12]2)[C:3]1=[O:28].Cl>O1CCOCC1>[C:22]([C:19]1[CH:20]=[CH:21][C:16]([NH:15][C@H:13]2[CH2:12][C@H:11]([N:4]3[C:5]4=[N:6][CH:7]=[CH:8][CH:9]=[C:10]4[C:2]([CH3:29])([CH3:1])[C:3]3=[O:28])[CH2:14]2)=[N:17][CH:18]=1)(=[O:23])[CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

3,3-Dimethyl-1-(trans-3-((5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)amino)cyclobutyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (68 mg, 0.172 mmol) was dissolved in dioxane (345 μl). Aqueous hydrochloric acid (2 M, 862 μl, 1.724 mmol) was added and the reaction mixture heated at 80° C. for 3 h. The reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous layer was back extracted with ethyl acetate and the combined organic layer was dried with sodium sulfate and concentrated. The crude product was purified silica chromatography eluting with a gradient of ethyl acetate in hexane (0-70%) to give 1-(trans-3-((5-acetylpyridin-2-yl)amino)cyclobutyl)-3,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (30 mg, 0.086 mmol, 49.7% yield) as white solid. M+1: 351.

Workup

customThe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate
extractionThe aqueous layer was back extracted with ethyl acetate
dry with materialthe combined organic layer was dried with sodium sulfate
concentrationconcentrated
customThe crude product was purified silica chromatography
washeluting with a gradient of ethyl acetate in hexane (0-70%)

Sources & evidence

ORD record: ord-4724ebae641c4bd58424b540244f9123
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174992B2

Reaction notes

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