Triethylamine → HCID 22032121, compound

HRID 1792534Notes

Reaction equation

HRID 1792534 reaction equation
[CH3:1][S:2]([C:5]1[S:9][C:8]([C:10]2[N:14]3[CH:15]=[C:16]([C:19]4[C:20]([C:43](O)=[O:44])=[N:21][N:22]([C:24]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH:23]=4)[CH:17]=[CH:18][C:13]3=[N:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl.C([N:49]=C=NCCCN(C)C)C.[Cl-].[NH4+].C(N(CC)CC)C>CN(C)C=O>[CH3:1][S:2]([C:5]1[S:9][C:8]([C:10]2[N:14]3[CH:15]=[C:16]([C:19]4[C:20]([C:43]([NH2:49])=[O:44])=[N:21][N:22]([C:24]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)[CH:23]=4)[CH:17]=[CH:18][C:13]3=[N:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22031104HCID 22031104, compound

Product 1

HCID 22032121HCID 22032121, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 40 mg 4-{3-[5-(methylsulfonyl)-2-thienyl]imidazo[1,2-a]pyridin-6-yl}-1-trityl-1H-3-pyrazole carboxylic acid, 37 mg 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride, 26 mg 1-oxybenzotriazole, 17 mg ammonium chloride, 0.077 mL triethylamine and 3 mL N,N-dimethylformamide was left overnight at room temperature. The solvent was evaporated, and the residue was purified by NH silica gel column chromatography (ethyl acetate/methanol) to give 22 mg 4-{3-[5-(methylsulfonyl)-2-thienyl]imidazo[1,2-a]-pyridin-6-yl}-1-trityl-1H-3-pyrazole carboxamide as colorless crystals. This product was subjected to deprotection of the trityl group in the same manner as in Example 79, to give 14 mg of the title compound as colorless crystals.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-543c024e55e247aa8686db2a50819f6a
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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