Aniline → HCID 70271866, compound

HRID 1422217Notes

Reaction equation

HRID 1422217 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]2)=[C:4]([CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([C:21](O)=[O:22])[CH2:17][CH2:16]2)[CH:3]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[C:25]1([NH:24][C:21]([CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][C:4]3[CH:3]=[C:2]([Br:1])[CH:11]=[C:10]4[C:5]=3[NH:6][C:7](=[O:13])[C:8](=[O:12])[NH:9]4)[CH2:16][CH2:17]2)=[O:22])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18706388HCID 18706388, compound

Product 1

HCID 70271866HCID 70271866, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

382 mg (1 mmol) of N-(7-bromo-2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-ylmethyl)-piperidine-4-carboxylic acid (Example 6), 186 mg (2 equiv.) of aniline, 480 mg (2.5 equiv.) of N-(3-dimethylaminopropyl)-N'-ethyl-carbodiimide hydrochloride and 384 mg (2.5 equiv.) of 1-hydroxy-benzotriazole are stirred at 20° C. in dried dimethylformamide for 48 hours. The mixture is poured into water and extracted three times with 100 ml of dichloromethane. The organic phases are combined and concentrated by evaporation. The residue is dissolved in 30 ml of dichloromethane and the solution is stirred for 30 minutes. The white solid is filtered off, washed with dichloromethane and dried.

Workup

  1. extractionextracted three times with 100 ml of dichloromethane
  2. concentrationconcentrated by evaporation
  3. dissolutionThe residue is dissolved in 30 ml of dichloromethane
  4. filtrationThe white solid is filtered off
  5. washwashed with dichloromethane
  6. customdried

Sources & evidence

ORD record
ord-d48f702eaf2946bbae26f7480cdafac6
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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