Hydrochloric Acid → HCID 90418576, compound

HRID 633537Notes

Reaction equation

[F:1][C:2]1([F:32])[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][C:11]=2[C:20]2[C:28]3[C:23](=[C:24]([O:29]C)[N:25]=[CH:26][CH:27]=3)[N:22]([CH3:31])[CH:21]=2)[CH2:4][CH2:3]1.Cl.O1CCOCC1>>[F:32][C:2]1([F:1])[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][C:11]=2[C:20]2[C:28]3[CH:27]=[CH:26][NH:25][C:24](=[O:29])[C:23]=3[N:22]([CH3:31])[CH:21]=2)[CH2:4][CH2:3]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 90416509HCID 90416509, compound

Product 1

HCID 90418576HCID 90418576, compoundYield 80.5%

Conditions

Temperature: 70 °C

Procedure

The product from Example 41A (0.1 g, 0.215 mmol) and 4 M hydrogen chloride in dioxane (5 mL, 20.00 mmol) were combined and heated at 70° C. for 24 hours, cooled and concentrated. Purification by chromatography (silica gel, 0-4% MeOH in dichloromethane) afforded the title compound (0.078 g, 80%). 1H NMR (300 MHz, DMSO-d6) δ ppm 10.96 (d, J=5.43 Hz, 1H) 7.86 (d, J=2.37 Hz, 1H) 7.79 (dd, J=8.65, 2.54 Hz, 1H) 7.55 (s, 1H) 7.33 (d, J=8.48 Hz, 1H) 6.88-6.95 (m, 1H) 6.43 (d, J=6.10 Hz, 1H) 4.12 (s, 3H) 4.04 (d, J=6.10 Hz, 2H) 3.20 (s, 3H) 1.60-2.12 (m, 7H) 1.24-1.41 (m, 2H). MS (ESI+) m/z 451 (M+H)+.

Workup

temperaturecooled
concentrationconcentrated
customPurification by chromatography (silica gel, 0-4% MeOH in dichloromethane)

Sources & evidence

ORD record: ord-ce08fab91c1046df8679c12f2cf379a7
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321764B2

Reaction notes

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