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

HRID 1921673Notes

Reaction equation

HRID 1921673 reaction equation
CO[C:3](=[C:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][C:21]1=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2([NH:13][C:14](=[O:19])[O:15][CH2:16][CH:17]=[CH2:18])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[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>[CH3:42][N:40]1[CH:41]=[C:37]([C:34]2[CH:35]=[CH:36][C:31]([NH:30][C:3](=[C:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[O:22][C:21]3=[O:29])[C:4]3[CH:9]=[CH:8][C:7]([C:10]4([NH:13][C:14](=[O:19])[O:15][CH2:16][CH:17]=[CH2:18])[CH2:11][CH2:12]4)=[CH:6][CH:5]=3)=[CH:32][CH:33]=2)[N:38]=[CH:39]1

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 Residue

Sources & evidence

ORD record
ord-db0419b988384a2497faa8fac93ad6e2
Source dataset
uspto-grants-2012_05
Patent number
US08173699B2

Reaction notes

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