Ammonium Chloride → 6-[4-(6-amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-1-[3-(1H-tetrazol-5-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1024623Notes

Reaction equation

HRID 1024623 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]([C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=4)[C:16](=[O:31])[C:17]4[CH:22]=[N:21][N:20]([C:23]5[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=5)[C:26]#[N:27])[C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N-:39]=[N+:40]=[N-:41].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:15]([C:32]4[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=4)[C:16](=[O:31])[C:17]4[CH:22]=[N:21][N:20]([C:23]5[CH:30]=[CH:29][CH:28]=[C:25]([C:26]6[NH:41][N:40]=[N:39][N:27]=6)[CH:24]=5)[C:18]=4[N:19]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 578994223-[6-[4-(6-Amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile

Product 1

HCID 1361896376-[4-(6-amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-1-[3-(1H-tetrazol-5-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-[6-[4-(5-amino-pyridin-2-yl)-phenyl]-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzonitrile (prepared as described in example 28, 0.375 g, 0.726 mmol) in N,N-dimethylformamide (7 mL), sodium azide (0.236 g, 3.63 mmol), ammonium chloride (0.19 g, 3.63 mmol) are added. The reaction mixture is then heated at 90° C. for 14 h. The reaction mixture is concentrated to a dry residue. It is purified by column chromatography to afford 6-[4-(6-amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-1-[3-(1H-tetrazol-5-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one. 1H NMR (DMSO-d6, 400 MHz) δ 8.81 (s, 1H), 8.57 (s, 1H), 8.50 (br, 1H), 8.38 (m, 1H), 8.27 (m, 1H), 8.07 (d, 1H), 7.79 (m, 2H), 7.55 (m, 2H), 7.39-7.46 (m, 5H), 6.59 (d, 1H), 6.54 (br, 1H); LC-MS calculated for C29H19ClN10O (M+H+) 559.1, found 559.1.

Workup

  1. concentrationThe reaction mixture is concentrated to a dry residue
  2. customIt is purified by column chromatography

Sources & evidence

ORD record
ord-589d0fda07864d4c8361a6db5e1eef9f
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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