Sodium Hydroxide → HCID 9838120, compound

HRID 1432321Notes

Reaction equation

HRID 1432321 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[CH:18]=[C:13]3[C:12]([C:28]#[N:29])=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[CH3:26][N:25]([CH3:27])[C:22]1[CH:21]=[CH:20][C:19]([C:17]2[CH:18]=[C:13]3[C:12]([C:28]#[N:29])=[CH:11][NH:10][C:14]3=[N:15][CH:16]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68954104HCID 68954104, compound

Product 1

HCID 9838120HCID 9838120, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2 (41.5 mg, 0.103 mmol) and 10% aqueous NaOH (2.0 mL) in EtOH (4.0 mL) was heated at 110° C. for 40 min. It was then poured onto water (5 mL), extracted with ethyl acetate (4×10 mL) and the combined organic extracts dried (MgSO4) and concentrated. The residue was purified by preparative TLC (PTLC) using 5% ethyl acetate in dichloromethane as eluent to give 3 as a light orange solid (14.9 mg, 36%); 1H NMR (400 MHz, CDCl3) δ 3.06 (s, 6H), 6.86 (d, J=8.9 Hz, 2H), 7.55 (d, J=8.9 Hz, 2H), 7.89 (s, 1H), 8.25 (d, J=2.0 Hz, 1H), 8.64 (bs, 1H); MS (CI) m/z 304.0 (MH+MeCN).

Workup

  1. additionIt was then poured onto water (5 mL)
  2. extractionextracted with ethyl acetate (4×10 mL)
  3. dry with materialthe combined organic extracts dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (PTLC)

Sources & evidence

ORD record
ord-b62c155749e24d79aeb4ad8898b31683
Source dataset
uspto-grants-2009_11
Patent number
US07612086B2

Reaction notes

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