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

HRID 2172904Notes

Reaction equation

HRID 2172904 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]([CH3:30])[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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]([CH3:30])[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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67007902N-{4-[(3-methoxyphenyl)(methyl)amino]-9H-pyrimido[4,5-b]indol-2-yl}-2,2-dimethylpropanamide

Product 1

HCID 25233119N4-(3-methoxyphenyl)-N4-methyl-9H-pyrimido[4,5-b]indole-2,4-diamineYield 93%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Using the general procedure described above, the reaction of 9 (90 mg, 0.22 mmol) and 1 N NaOH provided 66 mg of AAG105 as a white solid in 93% yield. TLC Rf 0.27 (chloroform-methanol 15:1); mp 245.3-245.7° C.; 1H NMR (DMSO-d6) δ 3.48 (s, 3H, OCH3), 3.71 (s, 3H, NCH3), 6.20 (s, 2H, NH2, exch), 5.75-7.15 (m, 8H, Ar—H), 11.22 (s, 1H, 9-NH, exch). Anal. Calculated (C18H17N5O. 0.17H2O): C, 67.05; H, 5.42; N, 21.72. Found: C, 67.06; H, 5.37; N, 21.56.

Workup

  1. customprovided 66 mg of AAG105 as a white solid in 93% yield

Sources & evidence

ORD record
ord-09f2c283f6504e8dbf70cbaba70f545d
Source dataset
uspto-grants-2015_06
Patent number
US09056869B2

Reaction notes

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