Pyridine → HCID 68811949, compound

HRID 1792530Notes

Reaction equation

HRID 1792530 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:60])[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]3[CH:25]=[C:26]([C:29]4[C:30]([C:53]5[CH:58]=[CH:57][C:56]([F:59])=[CH:55][CH:54]=5)=[N:31][N:32]([C:34]([C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=5)([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[CH:33]=4)[CH:27]=[CH:28][C:23]3=[N:22][CH:21]=2)=[CH:16][CH:15]=1.O1CCCC1.N1C=CC=CC=1>O>[C:1]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:60])[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]3[CH:25]=[C:26]([C:29]4[C:30]([C:53]5[CH:54]=[CH:55][C:56]([F:59])=[CH:57][CH:58]=5)=[N:31][N:32]([C:34]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)([C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=5)[C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[CH:33]=4)[CH:27]=[CH:28][C:23]3=[N:22][CH:21]=2)=[CH:16][CH:15]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 23537741HCID 23537741, compound

Product 1

HCID 68811949HCID 68811949, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.014 mL acetic anhydride was added to a solution mixture of 50 mg N1-(3-aminopropyl)-4-{6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}benzamide obtained in Example 43, 0.4 mL tetrahydrofuran and 0.2 mL pyridine under ice-cooling. The mixture was stirred at room temperature for 1 hour, water was added thereto, and the mixture was stirred for 30 minutes. The solvent was evaporated, and the residue was purified by NH silica gel column chromatography (acetic acid/methanol) to give 53 mg N1-[3-(acetylamino)propyl]-4-(6-[3-(4-fluorophenyl)-1-trityl-1H-4-pyrazolyl]imidazo[1,2-a]pyridin-3-yl}benzamide. This product was subjected to deprotection of the trityl group in the same manner as in Example 89, to give 27 mg of the title compound (colorless crystals; recrystallization solvent, methanol/diethyl ether).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe solvent was evaporated
  4. customthe residue was purified by NH silica gel column chromatography (acetic acid/methanol)

Sources & evidence

ORD record
ord-0afd9286cd364dabbada624a7974cb1d
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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