Sodium Hydroxide → 2-(3-((1-oxo-1-(10H-phenothiazin-10-yl)butan-2-yl)thio)-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid

HRID 63756Notes

Reaction equation

HRID 63756 reaction equation
[O:1]=[C:2]([N:26]1[C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[S:33][C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:3]([S:6][C:7]1[N:8]=[N:9][C:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]([CH2:19][C:20]([O:22]CC)=[O:21])[C:11]=2[N:25]=1)[CH2:4][CH3:5].[OH-].[Na+]>O1CCOCC1>[O:1]=[C:2]([N:26]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=2[S:33][C:34]2[C:39]1=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:3]([S:6][C:7]1[N:8]=[N:9][C:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]([CH2:19][C:20]([OH:22])=[O:21])[C:11]=2[N:25]=1)[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118221996HCID 118221996, compound

Product 1

HCID 1182220132-(3-((1-oxo-1-(10H-phenothiazin-10-yl)butan-2-yl)thio)-5H-[1,2,4]triazino[5,6-b]indol-5-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 28 (161 mg, 0.2901 mmol) was dissolved in 15 ml 1,4-dioxane and 0.58 ml 1 M NaOH was added to the solution. The reaction mixture was stirred at room temperature. After 14 h, TLC indicated that there was no starting material remained and the reaction was stopped. The pH of the reaction was adjusted to 4-5 using concentrated HAc. The mixture was extracted by ethyl acetate for three times and the organic phase was combined. The organic phase was dried by anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column (DCM/MeOH-60:1) and the viscous oil 29 was obtained. 1H NMR (500 MHz, CDCl3) δ 8.42 (d, J=8.0, 1H), 7.94 (br, 1H), 7.62-7.68 (m, 2H), 7.35-7.49 (m, 4H), 7.24-7.30 (m, 3H), 7.07 (br, 1H), 5.40 (t, J=7.0, 1H), 5.01 (s, 2H), 2.03 (br, 1H), 1.84 (br, 1H), 0.92 (br, 3H). HRMS calcd for C27H21N5O3S2527.1086. found 527.1093.

Workup

  1. concentrationusing concentrated HAc
  2. extractionThe mixture was extracted by ethyl acetate for three times
  3. dry with materialThe organic phase was dried by anhydrous Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column (DCM/MeOH-60:1)

Sources & evidence

ORD record
ord-9ebc7b06578548de9ed3d4609b48ce8c
Source dataset
uspto-grants-2016_09
Patent number
US09447103B2

Reaction notes

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