Sodium Hydroxide → HCID 25232947, compound

HRID 2167936Notes

Reaction equation

HRID 2167936 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][C:14]=3[N:13]=[C:12]([NH:23]C(=O)C(C)(C)C)[N:11]=2)=[CH:5][CH:4]=1.[OH-].[Na+].C(Cl)(Cl)Cl.CO>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][C:14]=3[N:13]=[C:12]([NH2:23])[N:11]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21584188Chloroform methanolHCID 67007923HCID 67007923, compound

Product 1

HCID 25232947HCID 25232947, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the general procedure described above, the reaction of 10 (80 mg, 0.20 mmol) and 1 N NaOH provided 40 mg of AAG106 as an off-white solid in 64% yield. TLC Rf 0.30 (chloroform-methanol 15:1); mp 208.9-209.1° C.; 1H NMR (DMSO-d6) δ 3.76 (s, 3H, OCH3), 6.19 (s, 2H, NH2, exch), 7.09-8.05 (m, 8H, Ar—H), 8.26 (s, 1H, 4-NH, exch), 11.27 (s, 1H, 9-NH, exch). Anal. Calculated (C17H15N5O. 0.35 CH3OH): C, 65.83; H, 5.22; N, 22.12. Found: C, 66.08; H, 5.22; N, 21.81.

Workup

  1. customprovided 40 mg of AAG106 as an off-white solid in 64% yield

Sources & evidence

ORD record
ord-0c858790e005440d85e740c4663fcff9
Source dataset
uspto-grants-2015_06
Patent number
US09045489B2

Reaction notes

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