Sodium Acetate → HCID 24821187, compound

HRID 1929527Notes

Reaction equation

HRID 1929527 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].Cl[C:9]1[N:14]=[N:13][C:12]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:31])=[C:20]([CH:30]=2)[C:21]([N:23]2[CH2:29][CH2:28][CH2:27][NH2+:26][CH2:25][CH2:24]2)=[O:22])=[C:11]([CH2:32][CH3:33])[CH:10]=1.CC([O-])=[O:36].[Na+]>CC(O)=O>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH2:32]([C:11]1[C:12]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:31])=[C:20]([CH:30]=2)[C:21]([N:23]2[CH2:29][CH2:28][CH2:27][NH2+:26][CH2:25][CH2:24]2)=[O:22])=[N:13][NH:14][C:9](=[O:36])[CH:10]=1)[CH3:33]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 86632297HCID 86632297, compound

Product 1

HCID 24821187HCID 24821187, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of B2, NaOAc (2 eq) and AcOH (0.16 M) was heated at reflux for 4 h. The reaction mixture was cooled down to RT and concentrated under reduced pressure. The crude was purified by preparative RP-HPLC, using H2O (0.1% TFA) and MeCN (0.1% TFA) as eluents (column: Water X-Terra C18). The pooled product fractions were lyophilized to give the title compound. 1H NMR (600 MHz, DMSO-d6) δ: 12.80 (1H, m), 8.84 (2H, s), 7.38-7.28 (3H, m), 6.66 (1H, s), 4.01 (2H, s), 3.85-3.7 (2H, m), 3.55 (1H, m), 3.36-3.32 (2H, m), 3.27 (1H, m), 3.20 (1H, m), 3.16 (1H, m), 2.45-2.42 (2H, m), 2.06 (1H, m), 1.90 (1H, m), 1.11-1.07 (3H, m). MS (ES) C19H23FN4O2 required: 358. found: 359 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. concentrationconcentrated under reduced pressure
  4. customThe crude was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-b1d2bb4ce2864408a27848942c3fbeeb
Source dataset
uspto-grants-2012_05
Patent number
US08188084B2

Reaction notes

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