Hydrochloric Acid → HCID 67954026, compound

HRID 1916850Notes

Reaction equation

HRID 1916850 reaction equation
C(OC([N:8]([C:22]1[N:23]=[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]2[C:30]=1[CH:31]([CH3:33])[CH3:32])[S:9]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)(=[O:11])=[O:10])=O)(C)(C)C.[ClH:34]>O1CCOCC1>[ClH:34].[CH:31]([C:30]1[N:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]2=[N:23][C:22]=1[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=1)(=[O:10])=[O:11])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67966860HCID 67966860, compound

Product 1

HCID 67954026HCID 67954026, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

To a solution of compound 4-F (0.230 g, 0.486 mmol) in dioxane (3 mL) was added 4N HCl in dioxane (10 mL) and the reaction mixture was stirred at room temperature for 1 day. An additional portion of 4N HCl in dioxane (5 mL) was added and the mixture stirred an additional two days at room temperature. The solvent was evaporated in vacuo, and the solid triturated in Et2O, collected by filtration, washed with Et2O and dried to afford compound 4-G as a yellow solid (0.196 g, 98%). 1H-NMR (CD3OD): δ 8.72 (d, J=6.8 Hz, 1H), 8.21 (d, J=8.6 Hz, 2H), 7.90-7.99 (m, 3H), 7.82 (d, J=9.0 Hz, 1H), 7.45-7.50 (m, 1H), 3.94 (s, 3H), 3.12-3.23 (m, 1H), 1.14 (d, J=7.1 Hz, 6H); MS: m/z 374.1 (MH+).

Workup

  1. stirringthe mixture stirred an additional two days at room temperature
  2. customThe solvent was evaporated in vacuo
  3. customthe solid triturated in Et2O
  4. filtrationcollected by filtration
  5. washwashed with Et2O
  6. customdried

Sources & evidence

ORD record
ord-5476a51dff4147f99acc49e272c67ce3
Source dataset
uspto-grants-2013_12
Patent number
US08618150B2

Reaction notes

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