Hydrochloric Acid → HCID 59118111, compound

HRID 432096Notes

Reaction equation

HRID 432096 reaction equation
C(OC([N:8]([CH2:25][C@H:26]1[CH2:35][CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:36]3[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=3)[C:39](O)=[O:40])[CH:32]=2)[O:27]1)[CH2:9][C@H:10]([O:17][Si](C(C)(C)C)(C)C)[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=O)(C)(C)C.CN(C1C=CC=CN=1)C.[CH3:54][S:55]([NH2:58])(=[O:57])=[O:56].Cl>C(Cl)Cl.O1CCOCC1>[OH:17][C@H:10]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:9][NH:8][CH2:25][C@H:26]1[CH2:35][CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:36]3[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=3)[C:39]([NH:58][S:55]([CH3:54])(=[O:57])=[O:56])=[O:40])[CH:32]=2)[O:27]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 218852-DimethylaminopyridineHCID 72879MethanesulfonamideHCID 60018253HCID 60018253, compound

Product 1

HCID 59118111HCID 59118111, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

The product of Example 86 (100 mg, 0.16 mmol), 1-[(3-dimethylamino)propyl]-3-ethylcarbodiimide (36 mg, 0.19 mmol), dimethylaminopyridine (20 mg, 0.16 mmol), and methylsulfonamide (17 mg, 0.18 mmol) were dissolved in 2 mL methylene chloride and stirred overnight at room temperature. The mixture was treated with 0.5 mL 4 M HCl in 1,4-dioxane was added, the solution stirred for 0.5 hours, concentrated to dryness and the residue was purified by preparative HPLC to obtain the title compound (47 mg, 62%). 1H NMR (CD3CN-d3) δ: 8.91 (s, 1H), 8.76 (d, 1H), 8.51 (d, 1H), 8.07 (s, 1H), 7.97 (t, 1H), 7.88-7.83 (m, 2H), 7.62-7.56 (m, 1H), 7.50-7.47 (m, 2H), 6.98 (d, 1H), 5.46 (d, 1H), 4.54-4.47 (m, 1H), 3.52 (dd, 2H), 3.37 (s, 3H), 3.39-3.25 (m, 2H), 2.99-2.90 (m, 2H), 2.14-2.09 (m, 1H), 1.86-1.79 (m, 1H). MH+=482.2

Workup

  1. additionwas added
  2. stirringthe solution stirred for 0.5 hours
  3. concentrationconcentrated to dryness
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-8b90fd3c18c34bde97ffe3e3035cd222
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

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