Acetic Acid → HCID 15719366, compound

HRID 1087241Notes

Reaction equation

HRID 1087241 reaction equation
[Br:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:19][C@H:18]([CH2:20][O:21]CC3C=CC=CC=3)[C@@H:13]([O:14]C(=O)C)[C@@H:12]2[F:29])=[C:4](Br)[N:3]=1.O.[OH-].[Li+].C(Cl)(Cl)Cl.CO.C(O)(=O)C.[NH3:44]>>[Br:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:13]([OH:14])[C@@H:12]2[F:29])=[C:4]([NH2:44])[N:3]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 222AmmoniaHCID 168937Lithium hydroxide, monohydrateHCID 21584188Chloroform methanolHCID 53825138HCID 53825138, compound

Product 1

HCID 15719366HCID 15719366, compound

Procedure

A solution of 1a (5.84 g, 10.5 mmol) in 400 mL of ethanolic ammonia (saturated at 0° C.) was sealed in a glass-lined stainless steel bomb and left at room temperature for 3 days. The solution was evaporated to dryness and evaporated with ethanol to remove ammonia. The residue, containing the desired product and 5'-benzoyl compound, was dissolved in 440 mL of acetonitrile and 120 mL of water. Lithium hydroxide monohydrate (881 mg, 21 mmol) was added, and the solution was stirred for 16 hours at room temperature. Thin-layer chromatography (5:1 CHCl3 -MeOH) indicated complete reaction. The chilled solution was carefully neutralized with glacial acetic acid and evaporated to dryness. The white solid residue was recrystallized from water. The product was dried in vacuo at room temperature at 100° C. for 2 hours: 2.15 g (59.2%). Mp 209-210° C., TLC 5:1 CHCl3 -MeOH Rf 0.47; HPLC 99.8% 9:1; H2O-MeCN; MS, 3.48 (M+1)+ ; UV λmax pH 1 264 (14.3), pH 7 264 (14.9), pH 13 264 (15.2). Anal. Calcd. for C10H11BrFN5O3 : C, 34.50; H, 3.18; N, 20.12. Found: C, 34.36; H, 3.28; N, 19.93.

Workup

  1. customThe solution was evaporated to dryness
  2. customevaporated with ethanol
  3. customto remove ammonia
  4. additionThe residue, containing the desired product and 5'-benzoyl compound
  5. dissolutionwas dissolved in 440 mL of acetonitrile
  6. customreaction
  7. customevaporated to dryness
  8. customThe white solid residue was recrystallized from water
  9. customThe product was dried in vacuo at room temperature at 100° C. for 2 hours

Sources & evidence

ORD record
ord-eccde478eb4a494eb93e505dd158f619
Source dataset
uspto-grants-1991_07
Patent number
US05034518

Reaction notes

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