3-Amino-1,2-propanediol, (S)- → (2S)-2-[(2,3-Dihydroxypropyl)amino]-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile

HRID 640726Notes

Reaction equation

HRID 640726 reaction equation
Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:21][CH3:22])[CH:8]=2)[N:3]=1.[OH:23][C@H:24]([CH2:27][OH:28])[CH2:25][NH2:26]>CC(O)C>[OH:23][C@H:24]([CH2:27][OH:28])[CH2:25][NH:26][C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:21][CH3:22])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 4409023-Amino-1,2-propanediol, (S)-2×HCID 113703952-Chloro-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 11337583(2S)-2-[(2,3-Dihydroxypropyl)amino]-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrileYield 22.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-chloro-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile (65.0 mg, 0.208 mmol) and (S)-2,3-dihydroxypropylamine (114 mg, 1.25 mmol) in 10 mL of 2-propanol was heated in a sealed tube at 120° C. for 63 hours. Another portion of (S)-2,3-dihydroxypropylamine was added (50 mg), and the reaction was stirred for another 12 hours. The solution was concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC to provide the titled product (17 mg, 22%). Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C20H19FN3O3 (M+H+): 368.1405. Found 368.1398.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customThe crude residue was purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-ae2ca26cfc2c4d3c91ba4731716fd34e
Source dataset
uspto-grants-2010_04
Patent number
US07692017B2

Reaction notes

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