Triethylamine → HCID 19875964, compound

HRID 1460544Notes

Reaction equation

HRID 1460544 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.[CH2:9]([N:11](CC)CC)[CH3:10].[I-].ClC1C=CC=C[N+]=1C.NCC[N:28]1[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:36]2[N:44]([CH2:45][C:46]3[O:47][C:48]([CH3:51])=[CH:49][CH:50]=3)[C:39]3=[N:40][CH:41]=[CH:42][CH:43]=[C:38]3[N:37]=2)[CH2:30][CH2:29]1>O.ClCCl>[CH3:51][C:48]1[O:47][C:46]([CH2:45][N:44]2[C:39]3=[N:40][CH:41]=[CH:42][CH:43]=[C:38]3[N:37]=[C:36]2[NH:35][C:31]2([CH2:10][CH2:9][NH:11][C:6]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)=[O:8])[CH2:32][CH2:33][CH2:34][NH:28][CH2:29][CH2:30]2)=[CH:50][CH:49]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 102683-Furoic acidHCID 1670692-Chloro-1-methylpyridinium iodideHCID 15037447HCID 15037447, compound

Product 1

HCID 19875964HCID 19875964, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 1.12 parts of 3-furancarboxylic acid, 2.02 parts of N,N-diethylethanamine and 195 parts of dichloromethane are added 2.6 parts of 2-chloro-1-methylpyridinium iodide at room temperature. After stirring for 1 hour, 3.3 parts of N-[1-(2-aminoethyl)hexahydro-1H-azepin-4-yl]-3-[(5-methyl-2-furanyl)methyl]-3H-imidazo[4,5-b]pyridin-2-amine are added and stirred overnight at room temperature. The mixture is poured into water and the layers are separated. The organic layer is dried, filtered and evaporated. The residue is purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 2.19 parts (36.1%) of N-[2-[hexahydro-4-[[3-[(5-methyl-2-furanyl)methyl]-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1H-azepin-4-yl]ethyl]-3-furancarboxamide as a residue (compound 190).

Workup

  1. stirringstirred overnight at room temperature
  2. customthe layers are separated
  3. customThe organic layer is dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated

Sources & evidence

ORD record
ord-d1bd3ce0c4f549f78e126d01fc024fed
Source dataset
uspto-grants-1991_12
Patent number
US05071846

Reaction notes

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