Sodium Hydroxide → N4-(3-methoxyphenyl)-9H-pyrimido[4,5-b]indole-2,4-diamine

HRID 2167934Notes

Reaction equation

HRID 2167934 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1.[OH-].[Na+].C(Cl)(Cl)Cl.CO>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21584188Chloroform methanolHCID 67008043N-{4-[(3-methoxyphenyl)amino]-9H-pyrimido[4,5-b]indol-2-yl}-2,2-dimethylpropanamide

Product 1

HCID 25233118N4-(3-methoxyphenyl)-9H-pyrimido[4,5-b]indole-2,4-diamineYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using the general procedure described above, the reaction of 8 (90 mg, 0.23 mmol) and 1 N NaOH provided 65 mg of AAG104 as a transparent solid in 92% yield. TLC Rf 0.34 (chloroform-methanol 15:1); mp 225.2-225.6° C.; 1H NMR (DMSO-d6) δ 3.74 (s, 3H, OCH3), 6.05 (s, 2H, NH2, exch), 6.88-8.07 (m, 8H, Ar—H), 8.16 (s, 1H, 4-NH, exch), 11.20 (s, 1H, 9-NH, exch). Anal. Calculated (C17H15N5O. 0.15 (C2H5)2O): C, 66.79; H, 5.25; N, 22.13. Found: C, 66.77; H, 5.08; N, 22.13.

Workup

  1. customprovided 65 mg of AAG104 as a transparent solid in 92% yield

Sources & evidence

ORD record
ord-9120a26d829741ee852623ee3347130e
Source dataset
uspto-grants-2015_06
Patent number
US09045489B2

Reaction notes

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