2-bromo-1-(5-bromo-2-methoxyphenyl)ethanone → HCID 25107258, compound

HRID 604881Notes

Reaction equation

HRID 604881 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:6]=1[O:12][CH3:13])=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH:28][C:29]([NH2:31])=[S:30])[CH:19]=[CH:20][C:21]=1[N:22]1[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]1>C(OCC)C>[Br:11][C:9]1[CH:8]=[CH:7][C:6]([O:12][CH3:13])=[C:5]([C:3]2[N:31]=[C:29]([NH:28][C:18]3[CH:19]=[CH:20][C:21]([N:22]4[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]4)=[C:16]([O:15][CH3:14])[CH:17]=3)[S:30][CH:2]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 27568502-bromo-1-(5-bromo-2-methoxyphenyl)ethanoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 25107258HCID 25107258, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared in analogy to example 1 step e) from 102 mg (0.33 mmol) 2-bromo-1-(5-bromo-2-methoxyphenyl)ethanone and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The crude reaction was diluted with diethyl ether and stirred for 15 minutes at room temperature. The product was filtered off and dried to yield 147 mg (99%) [4-(5-bromo-2-methoxy-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a white solid. MS ISP (m/e): 472.8/470.9 (100/93) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.74 (s, 1H), 9.30 (s, 1H), 8.34 (dd, 1H), 7.70 (s, 1H), 7.60 (s, 1H), 7.51 (d, 1H), 7.47 (d, 1H), 7.13 (d, 1H), 7.05 (d, 1H), 4.00 (s, 3H), 3.95 (s, 3H), 2.35 (s, 3H).

Workup

  1. customThe crude reaction
  2. filtrationThe product was filtered off
  3. customdried

Sources & evidence

ORD record
ord-87a73dcdbfe840f1898c3d87b681a1ee
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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