4-Bromo-3'-chlorobenzophenone → HCID 10113213, compound

HRID 1392981Notes

Reaction equation

HRID 1392981 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.Br[C:18]1[CH:32]=[CH:31][C:21]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)=[O:23])=[CH:20][CH:19]=1>>[Cl:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[C:22]([C:21]1[CH:31]=[CH:32][C:18]([NH:1][C:2]2[N:7]=[C:6]([C:8]3[N:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]4=[N:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)=[CH:19][CH:20]=1)=[O:23]

Participants

3

Reactant 2

HCID 27568674-Bromo-3'-chlorobenzophenoneHCID 691978644-(Imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine

Product 1

HCID 10113213HCID 10113213, compoundYield 21%

Procedure

The title compound was prepared from 2-amino-4-(imidazo-[1,2-a]pyridin-3-yl)pyrimidine and 4-bromo-3′-chlorobenzophenone following the general method of Example 2. The crude product was purified by column chromatography on silica gel using chloroform/ethanol, 99:1, as the eluent affording 51 mg (21% yield) of the title compound as a yellow solid: mp 194.7-196.7° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.26 (s, 1 H), 10.17 (d, J=7.0 Hz, 1 H), 8.69 (s, 1 H), 8.54 (d, J=5.4 Hz, 1 H), 8.01 (d, J=8.7Hz, 2 H), 7.83-7.79 (m, 3 H), 7.76-7.72 (m, 2 H), 7.70-7.66 (m, 1 H), 7.62-7.59 (m, 1 H), 7.56-7.51 (m, 2 H), 7.21 (t, J=6.9 Hz, 1 H); 13C NMR (400 MHz, DMSO-d6) δ 193.2, 159.3, 157.7, 157.4, 148.4, 145.7, 140.4, 139.4, 133.7, 132.0, 131.8, 130.8, 129.8, 129.1, 129.0, 128.3, 127.6, 121.3, 118.3, 117.8, 114.3, 108.8; MS (ESP) m/z 426 (M+1).

Workup

  1. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-07540b624074477cb06a4c5d826ddf5b
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

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