Phenol → 3-({6-bromo-2-fluoro-3-[(6-oxo-6,7-dihydro-1H-purin-1-yl)methyl]phenyl}oxy)-5-chlorobenzonitrile

HRID 1875247Notes

Reaction equation

HRID 1875247 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Br:9])=[CH:7][CH:8]=1.CN(/[CH:24]=[N:25]/[C:26]1[N:27]=[CH:28][NH:29][C:30]=1[C:31](OCC)=[O:32])C.C1(O)C=CC=CC=1>C(Cl)Cl>[Br:9][C:6]1[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])=[C:4]([F:20])[C:3]([CH2:2][N:1]2[C:31](=[O:32])[C:30]3[NH:29][CH:28]=[N:27][C:26]=3[N:25]=[CH:24]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 671971663-{[3-(Aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 87550540ethyl 4-[(E)-dimethylaminomethylideneamino]-1H-imidazole-5-carboxylate

Product 1

HCID 687393323-({6-bromo-2-fluoro-3-[(6-oxo-6,7-dihydro-1H-purin-1-yl)methyl]phenyl}oxy)-5-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in a manner similar to that described herein using 3-{[3-(aminomethyl)-6-bromo-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.15 g, 0.422 mmol), ethyl 4-{[(1E)-(dimethylamino)methylidene]amino}-1H-imidazole-5-carboxylate (0.098 g, 0.464 mmol) and phenol (0.052 g, 0.548 mmol) in DCM (2 mL) to give 0.070 (34%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.44 (s, 1H), 8.17 (s, 1H), 7.82 (s, 1H), 7.59 (d, 1H), 7.52 (s, 1H), 7.46 (s, 1H), 7.15 (t, 1H), 5.28 (s, 2H).

Workup

  1. customThe title compound was prepared in a manner similar to

Sources & evidence

ORD record
ord-1c4dd8aeb9434e2bbc9bafed5a8c2e6c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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