Hydrochloric Acid → Pirmagrel

HRID 2417807Notes

Reaction equation

HRID 2417807 reaction equation
Cl.C(OCC)C.Cl.[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[N:21]2[CH:22]=[N:23][CH:24]=[C:20]2[CH:19]=[CH:18][CH:17]=1)([OH:10])=[O:9]>C(#N)C>[C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[N:21]2[CH:22]=[N:23][CH:24]=[C:20]2[CH:19]=[CH:18][CH:17]=1)([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 166380755-(5-Carboxypentyl)imidazo[1,5-a]pyridine hydrochloride

Product 1

HCID 55390Pirmagrel

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The residue is partitioned between water and methylene chloride after pH is adjusted to 10. The aqueous solution is further washed with chloroform, acidified to pH 1 and again washed with ether and toluene. After pH is adjusted to 5.5, extraction with chloroform gives crude 5-(5-carboxypentyl)imidazo-[1,5-a]pyridine. A solution of the acid in 30 ml of acetonitrile is treated with 5N ethanolic hydrochloric acid. After addition of 25 ml of ethyl ether, 5-(5-carboxypentyl)imidazo[1,5-a]pyridine hydrochloride, melting at 201°-4°, crystallizes. 5-(5-Carboxypentyl)-imidazo[1,5-a]pyridine (example 2) is obtained on neutralization of a methanolic solution of the salt to pH 5.

Workup

  1. customcrystallizes

Sources & evidence

ORD record
ord-8c13edb20c02457eb70deb949672b44d
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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