Hydrochloric Acid → HCID 86288168, compound

HRID 633574Notes

Reaction equation

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

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 90415835HCID 90415835, compound

Product 1

HCID 86288168HCID 86288168, compoundYield 83%

Conditions

Temperature: 70 °C

Procedure

The product from Example 94A (0.052 g, 0.094 mmol) and 4 M hydrogen chloride in dioxane (5 mL, 20.00 mmol) were combined and heated at 70° C. for 4 hours, cooled and concentrated. Purification by chromatography (silica gel, 0-4% methanol in dichloromethane) afforded the title compound (0.042 g, 83%). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.09 (s, 1H) 7.60-7.64 (m, 2H) 7.41-7.53 (m, 1H) 7.21-7.32 (m, 2H) 7.06-7.16 (m, 1H) 6.81 (d, J=8.48 Hz, 1H) 6.57 (s, 1H) 4.51 (s, 2H) 4.13 (s, 3H) 2.92 (s, 3H) 2.35 (s, 3H) 2.18 (s, 3H). MS (ESI+) m/z 540 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-6da8be053f764dcebb16fb7e07aa536d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321764B2

Reaction notes

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