Benzene → HCID 178437536, compound

HRID 412723Notes

Reaction equation

HRID 412723 reaction equation
C(O[C:4]([CH:6]([C:8]1[NH:9][C:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:12][C:11]=2[N:26]=1)C)=O)C.[NH2:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][C:29]=1[NH:37][CH3:38].[CH3:39]N1C(=O)N(C)CCC1.C1C=CC=CC=1>CCOCC>[CH2:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][C:10]2[NH:9][C:8]([CH:6]([C:38]3[N:37]([CH3:39])[C:29]4[CH:30]=[C:31]([C:32]([OH:34])=[O:33])[CH:35]=[CH:36][C:28]=4[N:27]=3)[CH3:4])=[N:26][C:11]=2[CH2:12]1)=[O:17])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 185377634-Amino-3-(methylamino)benzoic acidHCID 178471175HCID 178471175, compound

Product 1

HCID 178437536HCID 178437536, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
185 °C

Procedure

A mixture comprising benzyl 2-(1-ethoxycarbonylethyl)-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate (6.37 g, 0.018 mol), 4-amino-3-(N-methylamino)benzoic acid (2.70 g, 0.016 mol) and DMPU (20 mL) was degassed briefly on a vacuum line, heated heated at 185° C. under nitrogen for 4 hours, cooled and combined with an equivalent volume of benzene. Ether was then added to the mixture to give a precipitate. The precipitate was isolated by filtration, dried briefly on a vacuum line and further purified by a reprecipitation from hot ethanol/water. The precipitate was isolated recovered by filtration and dried to provided 2-[1-(5-benzyloxycarbonyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-2-yl)ethyl]-3-methyl-3H-benzoimidazole-5-carboxylic acid (4.73 g, 58%); 1H-NMR (300 MHz, DMSO-d6) d ppm: 12.70 (br s, 1H), 11.80 (s, 1H), 8.15 (s, 1H), 7.78 (d, 1H, J=8.3 Hz), 7.64 (d, 1H, J=8.3 Hz), 7.31 (s, 5H), 5.09 (s, 2H), 4.66 (q, 1H, J=5.2 Hz), 4.32 (br s, 2H), 3.78 (s, 3H), 3.65 (br s, 2H), 2.52 (br s, 2H), 1.73 (d, 3H, J=5.2 Hz).

Workup

  1. temperatureheated
  2. temperaturecooled
  3. customto give a precipitate
  4. customThe precipitate was isolated by filtration
  5. customdried briefly on a vacuum line
  6. customfurther purified by a reprecipitation from hot ethanol/water
  7. customThe precipitate was isolated
  8. filtrationrecovered by filtration
  9. customdried

Sources & evidence

ORD record
ord-5df985f928024781b2be49ca8c3599cc
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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