Sodium Hydroxide → HCID 58692243, compound

HRID 2264271Notes

Reaction equation

HRID 2264271 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:22][CH2:21][N:20](C(=O)C)[CH2:19][CH2:18]3)[N:11]=2)=[CH:2]1.[OH-].[Na+]>C(O)(=O)C>[NH:20]1[CH2:21][CH2:22][CH:17]([NH:16][C:12]2[N:11]=[C:10]([C:3]3[C:4]4[C:5](=[N:6][CH:7]=[CH:8][CH:9]=4)[NH:1][CH:2]=3)[CH:15]=[CH:14][N:13]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58692219HCID 58692219, compound

Product 1

HCID 58692243HCID 58692243, compoundYield 188.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a flask was added compound 64 (20 mg) and 1 M aqueous NaOH (1 mL). The mixture was heated to 100° C. for 3 hrs. After being neutralized with acetic acid, the solution was concentrated and the residule was purified by reverse phase HPLC to afford 33 mg (71%) of the desired product. 1H NMR (300 MHz, CD3OD) δ 8.85 (m, 1 H), 8.60 (s, 1 H), 8.35 (d, 1 H), 8.10 (d, 1 H), 7.35 (m, 2 H), 4.40 (m, 1 H), 3.50 (m, 2 H), 3.30 (m, 2 H), 2.40 (m, 2 H), 1.95 (m, 2 H). MS (ESI) m/z: 295 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residule was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-fc976194392f4bbca0e33eb5ca4e07e0
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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