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

HRID 2167933Notes

Reaction equation

HRID 2167933 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][C:13]=3[N:12]=[C:11]([NH:22]C(=O)C(C)(C)C)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(Cl)(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][C:13]=3[N:12]=[C:11]([NH2:22])[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67007627N-{4-[(3-bromophenyl)amino]-9H-pyrimido[4,5-b]indol-2-yl}-2,2-dimethylpropanamide

Product 1

HCID 53283964-N-(3-bromophenyl)-9H-pyrimido[4,5-b]indole-2,4-diamineYield 76%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Using the general procedure described above, the reaction of 7 (209 mg, 0.47 mmol) and 1 N NaOH provided 128 mg of AAG103 as a white solid in 76% yield. TLC Rf 0.36 (chloroform-methanol 15:1); mp 233.6° C.; 1H NMR (DMSO-d6) δ 6.26 (s, 2H, NH2, exch), 7.09-8.09 (m, 8H, Ar—H), 8.44 (s, 1H, 4-NH, exch), 11.32 (s, 1H, 9-NH, exch). Anal. Calculated (C16H12BrN5): C, 54.25; H, 3.41; N, 19.77; Br, 22.55. Found: C, 54.38; H, 3.48; N, 19.56; Br, 22.29.

Workup

  1. customprovided 128 mg of AAG103 as a white solid in 76% yield

Sources & evidence

ORD record
ord-1364b92d70c44a75bceb8d9b19483553
Source dataset
uspto-grants-2015_06
Patent number
US09045489B2

Reaction notes

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