Hydrochloric Acid → HCID 90415851, compound

HRID 633542Notes

Reaction equation

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

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 90415710HCID 90415710, compound

Product 1

HCID 90415851HCID 90415851, compoundYield 15.4%

Conditions

Temperature: 70 °C

Procedure

The product from Example 46A (0.067 g, 0.15 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 reverse phase chromatography (C18, CH3CN/water (0.1% TFA), 10-100%) afforded the title compound (0.01 g, 15%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.97 (d, J=5.19 Hz, 1H) 7.80 (d, J=8.54 Hz, 2H) 7.45-7.61 (m, 5H) 6.87-6.95 (m, 1H) 6.54 (d, J=8.85 Hz, 1H) 6.48-6.53 (m, 1H) 6.23 (d, J=6.71 Hz, 1H) 4.48 (d, J=6.10 Hz, 2H) 4.14 (s, 3H) 3.07 (s, 3H). MS (ESI+) m/z 433 (M+H)+.

Workup

temperaturecooled
concentrationconcentrated
customPurification by reverse phase chromatography (C18, CH3CN/water (0.1% TFA), 10-100%)

Sources & evidence

ORD record: ord-bf93440232be451f9b417d1f363b1d7e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321764B2

Reaction notes

Loading…