Hydrochloric Acid → HCID 67048272, compound

HRID 1026838Notes

Reaction equation

HRID 1026838 reaction equation
[CH:1]1([S:4]([NH:7][C:8](=[O:46])[NH:9][C:10]2[CH:44]=[CH:43][C:13]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[N:29]=[CH:28][C:27]([CH2:30][N:31]([CH2:39][CH2:40][O:41][CH3:42])C(=O)OC(C)(C)C)=[CH:26][CH:25]=5)[S:23][C:16]=34)=[C:12]([F:45])[CH:11]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[F:45][C:12]1[CH:11]=[C:10]([NH:9][C:8]([NH:7][S:4]([CH:1]2[CH2:2][CH2:3]2)(=[O:5])=[O:6])=[O:46])[CH:44]=[CH:43][C:13]=1[O:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]2[CH:21]=[C:22]([C:24]3[CH:25]=[CH:26][C:27]([CH2:30][NH:31][CH2:39][CH2:40][O:41][CH3:42])=[CH:28][N:29]=3)[S:23][C:16]=12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 67048207HCID 67048207, compound

Product 1

HCID 67048272HCID 67048272, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 375 (140 mg, 0.208 mmol) in DCM (5 ml) was added HCl in dioxane (0.5 ml, 2 mmol, 9.6 eq, 4M in dioxane) and the reaction mixture was stirred for 4 hours. The mixture was diluted with EtOAc, made basic with NaHCO3 solution and extracted with EtOAc/acetone. The organic phase was collected and discarded. The aqueous phase was concentrated and the residue was suspended in a mixture of DCM and acetone. The solution phase was collected, dried with Na2SO4, filtered and concentrated to afford 376 as a beige solid after further trituration with Et2O (yield 8 mg, 7%). 1H NMR (DMSO-d6): 8.67 (s, 1H), 8.56 (s, 1H), 8.47 (d, J=5.28, 1H), 8.27 (s, 1H), 8.19 (d, J=8.02 Hz, 1H), 7.85 (m, 2H), 7.80 (s, 1H), 7.22 (m, 2H), 6.59 (d, J=5.28 Hz, 1H), 3.76 (s, 2H), 3.40 (m, 2H), 3.20 (s, 3H), 2.76 (m, 1H), 2.60 (m, 2H), 0.75 (m, 2H), 0.65 (m, 2H). LRMS (ESI): (calc.) 571.64 (found) 572.58 (MH)+.

Workup

  1. extractionextracted with EtOAc/acetone
  2. customThe organic phase was collected
  3. concentrationThe aqueous phase was concentrated
  4. additionthe residue was suspended in a mixture of DCM and acetone
  5. customThe solution phase was collected
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a02e145bf1824e4bbc05566f03adef53
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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