HCID 136197345, compound → HCID 136197376, compound

HRID 539866Notes

Reaction equation

HRID 539866 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][CH2:23][CH3:24])=[C:8]([C:10]2[NH:15][C:14](=[O:16])[C:13]([Br:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=2)[CH:9]=1)([O-])=O>Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][CH2:23][CH3:24])=[C:8]([C:10]2[NH:15][C:14](=[O:16])[C:13]([Br:17])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=2)[CH:9]=1

Participants

3

Reactant 1

HCID 136197345HCID 136197345, compound

Product 1

HCID 136197376HCID 136197376, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The compound (4.0 g, 10 mmol) of Example 33 was suspended in concentrated hydrochloric acid and heated to be refluxed. Reduced iron powder (1.7 g, 30 mmol) was added into the reaction mixture in batch, and stirred for 1 h. The hot reaction mixture was filtered and cooled to room temperature to generate a yellowish precipitate. After filtered, the solid was dried at 60° C. to give the hydrochlorate of the title compound (3.0 g, yield: 82%). 1H NMR (DMSO-d6) δ: 12.55 (1H, br), 10.18 (2H, br), 7.72 (1H, d), 7.50 (1H, dd), 7.27 (1H, d), 4.04 (2H, t), 3.39 (1H, m), 1.73 (2H, m), 1.17 (6H, d), 0.95 (3H, t).

Workup

  1. temperatureheated
  2. temperatureto be refluxed
  3. filtrationThe hot reaction mixture was filtered
  4. filtrationAfter filtered
  5. customthe solid was dried at 60° C.

Sources & evidence

ORD record
ord-aaf3b01c5a1b467fa133c42aec45a980
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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