5-methyl-4-(methylamino)methyl-1-triphenylmethyl-1H-imidazole → HCID 19900737, compound

HRID 1029512Notes

Reaction equation

HRID 1029512 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH2:26][NH:27]C.[CH3:29][CH:30]1[CH2:39][CH2:38][C:37]2[C:32]3=[C:33]([C:40]([C:42]([OH:44])=O)=[CH:41][N:31]13)[CH:34]=[CH:35][CH:36]=2>C(#N)C>[CH3:1][C:2]1[N:6]([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[N:4][C:3]=1[CH2:26][NH:27][C:42]([C:40]1[C:33]2=[C:32]3[C:37](=[CH:36][CH:35]=[CH:34]2)[CH2:38][CH2:39][CH:30]([CH3:29])[N:31]3[CH:41]=1)=[O:44]

Participants

4

Reactant 2

HCID 153083055-methyl-4-(methylamino)methyl-1-triphenylmethyl-1H-imidazoleHCID 199007324-methyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

Product 1

HCID 19900737HCID 19900737, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3.4 g (9.3 mmol) of 5-methyl-4-(methylamino) methyl-1-triphenylmethyl-1H-imidazole, 2.0 g (9.3 mmol) of 4-methyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid, and 2.06 g (10 mmol) of N,N-dicyclohexylcarbodiimide in 100 ml of acetonitrile was stirred for 12 hours under nitrogen. The precipitate was sucked off and the filtrate was evaporated in vacuo. The residue was dissolved in ethylacetate and washed with 2 N sodium hydroxide and saturated saline respectively, and then evaporated in vacuo. The residue was chromatographed on silicagel using methylene chloride/methanol (95/5) as an eluent. After evaporating the desired fractions 3.6 g of N-methyl, N-[(5-methyl-1-triphenylmethyl-1H-imidazol-4-yl)methyl]-4-methyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxamide were obtained.

Workup

  1. customthe filtrate was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ethylacetate
  3. washwashed with 2 N sodium hydroxide and saturated saline respectively
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silicagel
  6. customAfter evaporating the desired fractions 3.6 g of N-methyl

Sources & evidence

ORD record
ord-7ee14212a126443185592b0c574f4810
Source dataset
uspto-grants-1992_04
Patent number
US05102901

Reaction notes

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