Hydrochloric Acid → HCID 140539112, compound

HRID 1924454Notes

Reaction equation

HRID 1924454 reaction equation
[C:1]([C:5]1[C:6]([O:39][CH3:40])=[C:7]([CH:28]=[C:29]([N:31]2[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]2=[O:38])[CH:30]=1)/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][C:11]=1[CH2:21][NH:22]CCC(C)C)([CH3:4])([CH3:3])[CH3:2].[C:41](=O)(O)[O-:42].[Na+].Cl>CCO>[C:1]([C:5]1[C:6]([O:39][CH3:40])=[C:7]([CH:28]=[C:29]([N:31]2[CH:36]=[CH:35][C:34](=[O:37])[NH:33][C:32]2=[O:38])[CH:30]=1)[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])=[CH:12][C:11]=1/[CH:21]=[N:22]/[O:42][CH3:41])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 25234711HCID 25234711, compound

Product 1

HCID 140539112HCID 140539112, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the product from Example 30, Part A (35 mg, 0.070 mmol) in EtOH (2 ml) was added O-methoxylamine hydrochloride (29 mg, 0.35 mmol) and sodium bicarbonate (30 mg, 0.35 mmol). The resulting mixture was stirred at 70° C. for 2 h. To the mixture was added 1 N aq. HCl (1 ml) to give a colorless precipitate that was filtered and dried to give the title compound as a colorless solid (24 mg, 64%). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.43 (d, J=2.21 Hz, 1 H) 9.94 (s, 1 H) 8.74 (s, 1 H) 7.79-7.85 (m, 2 H) 7.76 (d, J=7.72 Hz, 1 H) 7.57-7.65 (m, 2 H) 7.32 (dd, J=8.64, 2.39 Hz, 1 H) 7.23 (d, J=2.57 Hz, 1 H) 7.18 (d, J=116.18 Hz, 1 H) 5.66 (dd, J=7.72, 2.21 Hz, 1 H) 3.93 (s, 3 H) 3.79 (s, 3 H) 3.03 (s, 3 H) 1.38 (s, 9 H).

Workup

  1. customto give a colorless precipitate that
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-3f661e47b2174439a498e0e3feab03bc
Source dataset
uspto-grants-2012_05
Patent number
US08178548B2

Reaction notes

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