4-Hydroxybenzoic Acid → HCID 66933487, compound

HRID 1928649Notes

Reaction equation

HRID 1928649 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[C:20]([NH2:22])[CH:19]=[N:18]2)=[CH:13][CH:12]=1.[OH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl>[OH:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:22][C:20]2[CH:19]=[N:18][N:17]([C:14]3[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:3]4[CH2:4][CH2:5][CH2:6][C@H:2]4[CH3:1])=[CH:12][CH:13]=3)[CH:21]=2)=[O:29])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59541708HCID 59541708, compound

Product 1

HCID 66933487HCID 66933487, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-ylamine obtained in Example 29-(1) (0.191 g), 4-hydroxybenzoic acid (0.097 g), 1-hydroxybenzotriazole monohydrate (0.107 g) and 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (0.18 g) in chloroform (6.4 mL) was stirred at room temperature for 4 days. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH-type silica gel column chromatography (eluting solvent: chloroform→chloroform:methanol=10:1) to give the titled compound (0.137 g) as a colorless amorphous substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by NH-type silica gel column chromatography (eluting solvent: chloroform→chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-cfc2ba60ce91480bb96e85500189ab7e
Source dataset
uspto-grants-2012_05
Patent number
US08183387B2

Reaction notes

Loading…