Hydrochloric Acid → HCID 67003502, compound

HRID 2362707Notes

Reaction equation

[I:1][C:2]1[N:23]([S:24]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=[CH:8][C:9]([C:10]3[S:14][C:13]([C:15]4([O:19]COC)[CH2:18][CH2:17][CH2:16]4)=[N:12][CH:11]=3)=[C:4]2[CH:3]=1.Cl>CO.O1CCCC1>[I:1][C:2]1[N:23]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=2)(=[O:26])=[O:25])[C:5]2=[N:6][CH:7]=[CH:8][C:9]([C:10]3[S:14][C:13]([C:15]4([OH:19])[CH2:18][CH2:17][CH2:16]4)=[N:12][CH:11]=3)=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 5-(2-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-(1-(methoxymethoxy)cyclobutyl) thiazole (Example 107B) (1.273 g, 2.138 mmol) in methanol (10.8 mL) and tetrahydrofuran (10.8 mL) was added 10% aqueous hydrochloric acid solution (6.61 mL, 21.38 mmol). The reaction mixture was heated to 65° C. for 3 hours. The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL). The layers separated, and the aqueous layer was extracted with additional ethyl acetate (2×50 mL). The combined organics were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound. MS APCI(+) m/z 552.54 (M+H)+.

Workup

customThe reaction was partitioned between ethyl acetate (50 mL) and water (50 mL)
customThe layers separated
extractionthe aqueous layer was extracted with additional ethyl acetate (2×50 mL)
dry with materialThe combined organics were dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f6f0aef0de2044f3a869b0f4d37e0e25
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691810B2

Reaction notes

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