HCID 58247411, compound → HCID 58247401, compound

HRID 1894167Notes

Reaction equation

HRID 1894167 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:17]([N+:18]([O-])=O)=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=2)=[CH:7][CH:6]=1)[CH3:2]>CC(O)=O.CO.[Zn]>[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:17]([NH2:18])=[CH:16][N:15]=[C:14]([Cl:21])[N:13]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 1

HCID 58247411HCID 58247411, compound

Product 1

HCID 58247401HCID 58247401, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of Compound 16a (2.12 g; 6.55 mmol) in AcOH (15 mL) and CH3OH (20 mL) was added Zn (2.57 g; 39.31 mmol) in portions at room temperature. The reaction mixture was stirred at room temperature for 6 h. The solid was collected by filtration and washed with CH3OH. The filtrate was concentrated. The residue was quenched with aqueous NaOH (<1 N) and adjusted to pH ˜7, and extracted with EtOAc (2×20 mL). The organic layer was dried over MgSO4 and concentrated. The crude product was purified by normal phase chromatography (SiO2) to give Compound 16b. 1H NMR (300 MHz, CDCl3): δ 8.15 (d, 2H), 7.95 (s, 1H), 7.25 (d, 2H), 4.45 (q, 2H), 1.4 (t, 3H); MS: m/z 294.1 (M+H)+.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with CH3OH
  3. concentrationThe filtrate was concentrated
  4. customThe residue was quenched with aqueous NaOH (<1 N)
  5. extractionextracted with EtOAc (2×20 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by normal phase chromatography (SiO2)

Sources & evidence

ORD record
ord-26e3006bc0c2404d8af788aa7e888806
Source dataset
uspto-grants-2013_08
Patent number
US08513271B2

Reaction notes

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