Hydrochloric Acid → HCID 68224035, compound

HRID 1400827Notes

Reaction equation

HRID 1400827 reaction equation
[CH:1]1([NH:4][C:5](=[O:43])[NH:6][C:7]2[CH:41]=[CH:40][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[CH:39]=[CH:38][C:24]([CH2:25][N:26]([CH2:34][CH2:35][O:36][CH3:37])C(=O)OC(C)(C)C)=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:42])[CH:8]=2)[CH2:3][CH2:2]1.Cl.O1CCOCC1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:1]1([NH:4][C:5]([NH:6][C:7]2[CH:41]=[CH:40][C:10]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([C:21]5[CH:39]=[CH:38][C:24]([CH2:25][NH:26][CH2:34][CH2:35][O:36][CH3:37])=[CH:23][CH:22]=5)[S:20][C:13]=34)=[C:9]([F:42])[CH:8]=2)=[O:43])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67451381HCID 67451381, compound

Product 1

HCID 68224035HCID 68224035, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 112 (560 mg, 0.923 mmol) in DCM (10 mL) was added 4.0M HCl in dioxane (0.923 mL, 3.69 mmol) and the reaction mixture was stirred at RT for 2 hours. The mixture was diluted with saturated NaHCO3 solution and the layers were separated. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The resultant solid was triturated with Et2O to afford title compound 113 (350 mg, 75% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.69 (s, 1H), 8.48 (d, J=5.48 Hz, 1H), 8.00 (s, 1H), 7.82 (d, J=8.41 Hz, 1H), 7.70 (m, 1H), 7.44 (d, J=8.22 Hz, 1H), 7.36 (t, J=9.19 Hz, 1H), 7.19 (m, 1H), 6.56 (m, 2H), 3.75 (s, 2H), 3.39 (t, J=5.67 Hz, 2H), 3.22 (s, 3H), 2.64 (t, J=5.67 Hz, 2H), 2.53 (m, 1H), 0.63 (m, 2H), 0.41 (m, 2H). MS (m/z)=507.5 (M+H).

Workup

  1. customthe layers were separated
  2. customThe organic phase was collected
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant solid was triturated with Et2O

Sources & evidence

ORD record
ord-7097cc4c061246e792c5345f51c46ec6
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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