Hydrochloric Acid → HCID 24856948, compound

HRID 1509970Notes

Reaction equation

HRID 1509970 reaction equation
Cl.O1CCOCC1.[NH2:8][C:9]1[N:18]=[C:17]([NH2:19])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:21][NH:22][C:23]3[CH:45]=[C:44]([O:46][CH3:47])[C:26]([O:27][CH2:28][C:29]([NH:31][C@H:32]([C:37]([O:39]C(C)(C)C)=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])=[C:25]([O:48][CH3:49])[CH:24]=3)[C:15]=2[CH3:20])[N:10]=1>O>[NH2:8][C:9]1[N:18]=[C:17]([NH2:19])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:21][NH:22][C:23]3[CH:45]=[C:44]([O:46][CH3:47])[C:26]([O:27][CH2:28][C:29]([NH:31][C@H:32]([C:37]([OH:39])=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])=[O:30])=[C:25]([O:48][CH3:49])[CH:24]=3)[C:15]=2[CH3:20])[N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 24856949HCID 24856949, compound

Product 1

HCID 24856948HCID 24856948, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

HCl in dioxane (3.22 ml, 12.87 mmol) was added to example (6) (0.03 g, 0.051 mmol) followed by a few drops of water. The solution was allowed to stir at RT. After 3 h, the solvents were evaporated, the residue triturated with Et2O and dried under vacuum to afford the title compound (7) (22 mg, 82%). LCMS purity 96%, m/z 527 [M+H]+, 1H NMR (400 MHz, d6-DMSO) δ: 12.6 (1H, s), 9.0 (1H, s), 8.0 (1H, d, J=8.3 Hz), 7.9 (1H, s), 7.5 (3H, m), 7.2 (1H, d, J=8.8 Hz), 6.0 (2H, s), 4.3 (3H, m), 4.2 (2H, d, J=5.4 Hz), 3.7 (6H, s), 2.7 (3H, s), 1.5 (3H, m), 0.8 (6H, m).

Workup

  1. customthe solvents were evaporated
  2. customthe residue triturated with Et2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-046a3f4255fe4724a37c2047377c52df
Source dataset
uspto-grants-2012_07
Patent number
US08211900B2

Reaction notes

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