Hydrochloric Acid → HCID 86288110, compound

HRID 633570Notes

Reaction equation

[F:1][C:2]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][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:27]C)[N:21]=[C:22]([CH2:25][CH3:26])[CH:23]=2)[N:18]([CH3:29])[CH:17]=1.Cl.O1CCOCC1>>[F:1][C:2]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12]([CH3:15])(=[O:13])=[O:14])=[CH:7][C:6]=1[C:16]1[C:24]2[CH:23]=[C:22]([CH2:25][CH3:26])[NH:21][C:20](=[O:27])[C:19]=2[N:18]([CH3:29])[CH:17]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 90416203HCID 90416203, compound

Product 1

HCID 86288110HCID 86288110, compoundYield 90.3%

Conditions

Temperature: 70 °C

Procedure

The product from Example 92B (0.04 g, 0.082 mmol) and 4M hydrogen chloride in dioxane (5 mL, 20.00 mmol) were combined, heated at 70° C. for 3 hours, cooled and concentrated. Purification by chromatography (silica gel, 0-4% methanol in dichloromethane) afforded the title compound (0.035 g, 90%). 1H NMR (300 MHz, DMSO-d6) δ ppm 10.87 (s, 1H) 7.58 (d, J=2.03 Hz, 1H) 7.49 (s, 1H) 7.41-7.52 (m, 1H) 7.17-7.28 (m, 2H) 7.05-7.14 (m, 1H) 6.82 (d, J=8.14 Hz, 1H) 6.38 (s, 1H) 4.51 (s, 2H) 4.07 (s, 3H) 2.94 (s, 3H) 2.43 (q, J=7.63 Hz, 2H) 1.14 (t, J=7.46 Hz, 3H). MS (ESI+) m/z 473 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-be03aa625e7f49a5a2c41151d5d1b68a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321764B2

Reaction notes

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