Hydrochloric Acid → HCID 90415587, compound

HRID 633523Notes

Reaction equation

[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[O:4][C:5]1[C:10]([C:11]2[C:19]3[C:14](=[C:15]([O:20]C)[N:16]=[CH:17][CH:18]=3)[N:13]([CH3:22])[CH:12]=2)=[CH:9][C:8]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[C:7]([F:28])[CH:6]=1.Cl.O1CCOCC1>>[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[O:4][C:5]1[C:10]([C:11]2[C:19]3[CH:18]=[CH:17][NH:16][C:15](=[O:20])[C:14]=3[N:13]([CH3:22])[CH:12]=2)=[CH:9][C:8]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[C:7]([F:28])[CH:6]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 90417690HCID 90417690, compound

Product 1

HCID 90415587HCID 90415587, compoundYield 68.5%

Conditions

Temperature: 70 °C

Procedure

The product from Example 11E (0.120 g, 0.252 mmol) and 4 M hydrogen chloride in dioxane (10 mL, 40.0 mmol) were combined and heated at 70° C. for 24 hours, cooled and concentrated. The residue was purified by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%) to afford the title compound (0.080 g, 68%). 1H NMR (300 MHz, DMSO-d6) δ ppm 10.95 (d, J=5.43 Hz, 1H) 9.57 (s, 1H) 7.41-7.55 (m, 3H) 7.23-7.34 (m, 1H) 7.05-7.15 (m, 1H) 6.86-6.93 (m, 1H) 6.79 (d, J=11.19 Hz, 1H) 6.51 (d, J=5.76 Hz, 1H) 4.09 (s, 3H) 3.03 (s, 3H). MS (ESI+) m/z 464 (M+H)+.

Workup

temperaturecooled
concentrationconcentrated
customThe residue was purified by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%)

Sources & evidence

ORD record: ord-f137bacc3e8b4fcda8cb417f7b15f7fa
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321764B2

Reaction notes

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