Hydrochloric Acid → HCID 59753838, compound

HRID 1453731Notes

Reaction equation

HRID 1453731 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[N:18]2[CH2:27][C:28]2[C:29]([CH3:34])=[N:30][O:31][C:32]=2[CH3:33])=[C:9]1[CH3:35])(C)(C)C.[OH-].[Na+].Cl>CCO>[CH3:34][C:29]1[C:28]([CH2:27][N:18]2[C:19](=[O:26])[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]2[C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:7][C:6]([OH:36])=[O:5])[C:9]=2[CH3:35])=[C:32]([CH3:33])[O:31][N:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67316270HCID 67316270, compound

Product 1

HCID 59753838HCID 59753838, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

The crude product of step b) was dissolved in 3 mL EtOH and treated with 0.5 mL of 1 M NaOH. After heating to 70° C. for 1 h, the reaction was cooled, acidified with 1 M HCl and extracted into DCM. The extracts were concentrated and the title compound was purified by preparative LCMS to give the title compound. 1H NMR (DMSO-d6) δ 7.84-7.81 (m, 1H), 7.56-7.46 (m, 2H), 7.25 (d, J=8.1 Hz, 1H), 7.19-7.16 (m, 1H), 6.93 (t, J=7.5 Hz, 1H), 6.69 (t, J=7.5 Hz, 1H), 6.39 (d, J=7.8 Hz, 1H), 3.73 (s, 1H), 4.85 (d, J=15.2 Hz, 1H), 4.52 (d, J=17.1 Hz, 1H), 4.51 (d, J=17.1 Hz, 1H), 3.51 (d, J=15.3 Hz, 1H), 2.35 (s, 3H), 2.07 (s, 3H), 2.02 (s, 3H); MS: ESI (negative): 428.6 (M−H).

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted into DCM
  3. concentrationThe extracts were concentrated
  4. customthe title compound was purified by preparative LCMS

Sources & evidence

ORD record
ord-d99c2597787a457e8732cc7f73452cc7
Source dataset
uspto-grants-2009_01
Patent number
US07476667B2

Reaction notes

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