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

HRID 1875246Notes

Reaction equation

HRID 1875246 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]([Br:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl: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:19][C:17]1[CH:16]=[C:13]([CH:12]=[C:11]([O:10][C:5]2[C:6]([Cl:9])=[CH:7][CH:8]=[C:3]([CH2:2][N:1]3[C:31](=[O:32])[C:30]4[NH:29][CH:28]=[N:27][C:26]=4[N:25]=[CH:24]3)[C:4]=2[F:20])[CH:18]=1)[C:14]#[N:15]

Participants

5

Reactant 3

HCID 996PhenolHCID 68485937HCID 68485937, compoundHCID 87550540ethyl 4-[(E)-dimethylaminomethylideneamino]-1H-imidazole-5-carboxylate

Product 1

HCID 687232323-bromo-5-({6-chloro-2-fluoro-3-[(6-oxo-6,7-dihydro-1H-purin-1-yl)methyl]phenyl}oxy)benzonitrileYield 38.1%

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-chloro-2-fluorophenyl]oxy}-5-bromobenzonitrile (0.61 g, 1.715 mmol), ethyl 4-{[(1E)-(dimethylamino)methylidene]amino}-1H-imidazole-5-carboxylate (0.397 g, 1.887 mmol) and phenol (0.484 g, 5.15 mmol) in DCM (3 mL) to give 0.31 g (38%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.58 (br. s., 1H), 8.45 (s, 1H), 8.17 (br. s., 1H), 7.93 (s, 1H), 7.58 (d, 2H), 7.47 (d, 1H), 7.21 (t, 1H), 5.30 (s, 2H). LCMS m/z 474.1 (M−H).

Workup

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

Sources & evidence

ORD record
ord-03533dd59e1b407c922bb2856259d49a
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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