Aniline → HCID 66778071, compound

HRID 406309Notes

Reaction equation

HRID 406309 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[N:20]=[C:12]3[CH:13]([C:17](O)=[O:18])[CH2:14][CH2:15][CH2:16][N:11]3[N:10]=2)[CH:6]=[CH:5][C:4]=1[N:21]1[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.O.C(OCC)(=O)C>[C:28]1([NH:27][C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][N:11]3[N:10]=[C:9]([C:7]4[CH:6]=[CH:5][C:4]([N:21]5[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]5)=[C:3]([O:2][CH3:1])[N:8]=4)[N:20]=[C:12]23)=[O:18])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

9

Reactant 5

HCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66777587HCID 66777587, compound

Product 1

HCID 66778071HCID 66778071, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine-8-carboxylic acid obtained in Preparation Example 5-1 (25 mg) was dissolved in N,N-dimethylformamide (0.5 mL). Aniline (7.2 mg), 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (40.6 mg), 1-hydroxybenzotriazole (28.6 mg) and N,N-diisopropylethylamine (75.7 μL) were sequentially added and the mixture was stirred at room temperature for five hours. Ethyl acetate and water were added to the reaction solution, and the organic layer and the aqueous layer were separated. The aqueous layer was further extracted with ethyl acetate. The resulting organic layers were combined, sprayed with nitrogen gas and concentrated. The residue was purified by NH silica gel column chromatography to obtain the title compound (14.1 mg). The compound was further separated by CHIRALPAK™ IA (2 cm×25 cm; mobile phase:hexane:ethanol=50:50) to obtain the title compound with a retention time of 7.6 minutes (4.5 mg). The property values of the compound are as follows.

Workup

  1. customthe organic layer and the aqueous layer were separated
  2. extractionThe aqueous layer was further extracted with ethyl acetate
  3. concentrationconcentrated
  4. customThe residue was purified by NH silica gel column chromatography

Sources & evidence

ORD record
ord-588bda9f48db485b99fd5157503ad265
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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