Hydrochloric Acid → HCID 67048272, compound

HRID 409992Notes

Reaction equation

HRID 409992 reaction equation
C(OC(=O)[N:7]([CH2:12][C:13]1[CH:14]=[N:15][C:16]([C:19]2[S:27][C:26]3[C:21](=[N:22][CH:23]=[CH:24][C:25]=3[O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:38][S:39]([CH:42]4[CH2:44][CH2:43]4)(=[O:41])=[O:40])=[O:37])=[CH:31][C:30]=3[F:45])[CH:20]=2)=[CH:17][CH:18]=1)[CH2:8][CH2:9][O:10][CH3:11])(C)(C)C.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[F:45][C:30]1[CH:31]=[C:32]([NH:35][C:36]([NH:38][S:39]([CH:42]2[CH2:43][CH2:44]2)(=[O:40])=[O:41])=[O:37])[CH:33]=[CH:34][C:29]=1[O:28][C:25]1[CH:24]=[CH:23][N:22]=[C:21]2[CH:20]=[C:19]([C:16]3[CH:17]=[CH:18][C:13]([CH2:12][NH:7][CH2:8][CH2:9][O:10][CH3:11])=[CH:14][N:15]=3)[S:27][C:26]=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-9e83e3479316444a85efac1b0154d8ac
Source dataset
uspto-grants-2014_06
Patent number
US08759522B2

Reaction notes

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