2-Bromo-3'-chloroacetophenone → [4-(3-Chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 604883Notes

Reaction equation

HRID 604883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](=O)[CH2:6]Br.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:26][C:27]([NH2:29])=[S:28])[CH:17]=[CH:18][C:19]=1[N:20]1[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]1>C(Cl)Cl.C(OCC)C.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:29]=[C:27]([NH:26][C:16]3[CH:17]=[CH:18][C:19]([N:20]4[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]4)=[C:14]([O:13][CH3:12])[CH:15]=3)[S:28][CH:6]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 387382-Bromo-3'-chloroacetophenoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 86624681[4-(3-Chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amineYield 100%

Reagents, catalysts & solvents 1

HCID 18956944Methylene chloride diethyl ether ethanolSolvent

Procedure

The title compound was prepared in analogy to example 1 step e) from 77 mg (0.33 mmol) 3-chlorophenacylbromide and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The solvent was evaporated under reduced pressure and the crude reaction was stirred with methylene chloride/diethyl ether/ethanol for 15 minutes at room temperature. The product was filtered off and dried to yield 118 mg (100%) [4-(3-chloro-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a light yellow solid. MS ISP (m/e): 397.1/399.2 (100/46) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.78 (s, 1H), 9.29 (s, 1H), 8.10 (s, 1H), 8.01 (s, 1H), 7.90 (d, 1H), 7.69 (s, 1H), 7.64 (s, 1H), 7.52 (d, 1H), 7.48 (t, 1H), 7.38 (d, 1H), 7.24 (d, 1H), 3.95 (s, 3H), 2.35 (s, 3H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe crude reaction
  3. filtrationThe product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-6d1d06789fd246d4b5cd690d4183d4fc
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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