4-(1-methyl-1H-imidazol-4-yl)aniline → HCID 178459817, compound

HRID 2240639Notes

Reaction equation

HRID 2240639 reaction equation
[CH2:1]([O:4][C:5](=[O:29])[NH:6][C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16](OC)=[C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[O:19][C:18]3=[O:26])=[CH:12][CH:11]=2)[CH2:9][CH2:8]1)[CH:2]=[CH2:3].[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:38]=[CH:39][N:40]([CH3:42])[CH:41]=2)=[CH:33][CH:32]=1>CN1C(=O)N(C)CCC1.C(OCC)(=O)C>[CH2:1]([O:4][C:5](=[O:29])[NH:6][C:7]1([C:10]2[CH:15]=[CH:14][C:13]([C:16]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([C:37]4[N:38]=[CH:39][N:40]([CH3:42])[CH:41]=4)=[CH:35][CH:36]=3)=[C:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[O:19][C:18]3=[O:26])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 188003164-(1-methyl-1H-imidazol-4-yl)anilineHCID 72252277Allyl (1-{4-[methoxy-(2-oxobenzofuran-3-ylidene)methyl]phenyl}cyclopropyl)-carbamate

Product 1

HCID 178459817HCID 178459817, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

1.05 g of allyl(1-{4-[methoxy-(2-oxobenzofuran-3-ylidene)methyl]phenyl}cyclopropyl)-carbamate and 0.47 g of 4-(4-aminophenyl)-1-methylimidazole in 3 mL of DMPU were reacted in the microwave reactor at 180° C. After cooling, the mixture was diluted to 150 mL with ethyl acetate, extracted 2× with water, and the organic phase was dried over MgSO4 and evaporated down to the residue with silica gel. The substance was chromatographed with dichloromethane/methanol (97:3) on silica gel 70 at a flow rate of 30 mL/min. Residue: 0.6 g of yellow oil.

Workup

  1. temperatureAfter cooling
  2. extractionextracted 2× with water
  3. dry with materialthe organic phase was dried over MgSO4
  4. customevaporated down to the residue with silica gel
  5. customThe substance was chromatographed with dichloromethane/methanol (97:3) on silica gel 70 at a flow rate of 30 mL/min

Sources & evidence

ORD record
ord-5f3c8d0b4fb2459da79b934afe6d440b
Source dataset
uspto-grants-2010_05
Patent number
US07723381B2

Reaction notes

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