Dibutyltin oxide → N-[2-methyl-5-(1H-tetrazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide

HRID 2402509Notes

Reaction equation

HRID 2402509 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:35])=[C:7]([NH:9][C:10](=[O:34])[C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:13][CH:12]=2)[CH:8]=1)#[N:2].C[Si]([N:40]=[N+:41]=[N-:42])(C)C.C([Sn](=O)CCCC)CCC>C(COC)OC>[CH3:35][C:6]1[CH:5]=[CH:4][C:3]([C:1]2[NH:42][N:41]=[N:40][N:2]=2)=[CH:8][C:7]=1[NH:9][C:10](=[O:34])[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[N:27]=[C:26]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57662918N-(5-cyano-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide

Product 1

HCID 136104297N-[2-methyl-5-(1H-tetrazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamideYield 81%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of N-(5-cyano-2-methylphenyl)-4-[(4-phenylquinazolin-2-yl)amino]benzamide (273 mg, 0.600 mmol), prepared as described in Example 10, trimethylsilylazide (160 μL, 1.2 mmol), and dibutyltin oxide (36 mg, 0.060 mmol) in dimethoxyethane (6 mL) was reacted in the microwave reactor (120° C., 100 psi, 2). The reaction was then concentrated on a rotary evaporator and the residue was purified by preparative reverse phase HPLC to give N-[2-methyl-5-(1H-tetrazol-5-yl)phenyl]-4-[(4-phenylquinazolin-2-yl)amino]benzamide (242 mg, 81%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.36 (s, 1H), 9.91 (s, 1H), 8.20 (d, 2H), 8.13 (d, 1H), 8.03 (d, 2H), 7.91-7.79 (m, 5H), 7.67-7.63 (m, 3H), 7.53 (d, 1H), 7.42 (ddd, 1H), 2.36 (s, 3H). MS (EI) for C29H22N8O: 499.3 (MH+).

Workup

  1. customprepared
  2. customwas reacted in the microwave reactor (120° C., 100 psi, 2)
  3. concentrationThe reaction was then concentrated on a rotary evaporator
  4. customthe residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-8535f7b412324a7f95726ea56ffd358f
Source dataset
uspto-grants-2014_08
Patent number
US08796294B2

Reaction notes

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