3,4-Diaminopyridine → HCID 178525444, compound

HRID 266834Notes

Reaction equation

HRID 266834 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:34]=[CH:33][C:13]([C:14]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][C:23]3=[O:24])[CH2:18][CH2:17]2)=[O:15])=[CH:12][CH:11]=1)([OH:3])=[O:2].[NH2:35][C:36]1[CH:37]=[N:38][CH:39]=[CH:40][C:41]=1[NH2:42].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH3:57]S(O)(=O)=O.[OH-].[Na+]>>[NH:42]1[C:41]2[CH:40]=[CH:39][N:38]=[CH:37][C:36]=2[N:35]=[C:57]1[CH:4]([C:1]([OH:3])=[O:2])[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:34]=[CH:33][C:13]([C:14]([N:16]2[CH2:17][CH2:18][CH:19]([N:22]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][C:23]3=[O:24])[CH2:20][CH2:21]2)=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 5

HCID 59183,4-DiaminopyridineHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 190310461-{1-[4-(5-Carboxypentyloxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril

Product 1

HCID 178525444HCID 178525444, compound

Procedure

To 1-{1-[4-(5-carboxypentyloxy)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (2.00 g) are added 3,4-diaminopyridine (0.47 g), phosphorus pentoxide (1.00 g) and methanesulfonic acid (7.0 ml) and the mixture is stirred with heating at 100°-120° C. for 3 hours. After cooling, the reaction solution is poured into ice-water (30 ml) and the mixture is adjusted to around pH 11 with aqueous sodium hydroxide solution and extracted with dichloromethane. The extract is dried with magnesium sulfate and the solvent is distilled off. The resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=20:1→9:1) to give 1-{1-[4-(5-(imidazo[4,5-c]pyridine-2-yl)carboxypentyloxy)benzoyl]-4-piperidinyl]-3,4-dihydrocarbostyril (1.32 g) as white amorphous form.

Workup

  1. temperaturewith heating at 100°-120° C. for 3 hours
  2. temperatureAfter cooling
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract is dried with magnesium sulfate
  5. distillationthe solvent is distilled off
  6. customThe resulting residue is purified by silica gel column chromatography (solvent: dichloromethane:methanol=20:1→9:1)

Sources & evidence

ORD record
ord-435a73bbf412487a9679ff0200a53872
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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