Hydrochloric Acid → HCID 86287895, compound

HRID 633548Notes

Reaction equation

HRID 633548 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[C:23]2[C:18](=[C:19]([O:24]C)[N:20]=[CH:21][CH:22]=2)[N:17]([CH3:26])[CH:16]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[C:23]2[CH:22]=[CH:21][NH:20][C:19](=[O:24])[C:18]=2[N:17]([CH3:26])[CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90416613HCID 90416613, compound

Product 1

HCID 86287895HCID 86287895, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

The product from Example 51D (0.116 g, 0.26 mmol) and 4 M hydrogen chloride (5 mL, 20.0 mmol) in dioxane 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 (0.051 g, 45%). 1H NMR (300 MHz, DMSO-d6) δ ppm 10.99 (d, J=5.09 Hz, 1H) 7.96 (d, J=2.37 Hz, 1H) 7.66 (dd, J=8.82, 2.37 Hz, 1H) 7.64 (s, 1H) 7.46-7.57 (m, 1H) 7.35-7.43 (m, 1H) 7.33 (s, 2H) 7.12-7.21 (m, 1H) 6.94 (d, J=6.78 Hz, 1H) 6.90 (d, J=8.48 Hz, 1H) 6.55 (d, J=6.10 Hz, 1H) 4.12 (s, 3H). MS (ESI+) m/z 432 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-abe29ccc4cae4ba19698390da12e8285
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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