4-Chloroaniline → HCID 24958478, compound

HRID 2196586Notes

Reaction equation

HRID 2196586 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][N:12]2[CH2:21][CH2:20][C:19]3[C:18]([C:22]([OH:24])=O)=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:13]2)=[CH:3][CH:2]=1.[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:22]([C:18]2[C:19]3[CH2:20][CH2:21][N:12]([CH2:11][C:4]4[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=[CH:2][CH:3]=4)[CH2:13][C:14]=3[CH:15]=[CH:16][CH:17]=2)=[O:24])=[CH:28][CH:27]=1

Participants

7

Reactant 5

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69047243HCID 69047243, compound

Product 1

HCID 24958478HCID 24958478, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid (80 mg, 0.251 mmol) was suspended in N,N-dimethylformamide (1.2 mL) then added 4-chloroaniline (45 mg, 0.351 mmol), 1-hydroxy-7-azabenzotriazole (34 mg, 0.251 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (72 mg, 0.376 mmol) and N,N-diisopropylethylamine (89 mg, 0.878 mmol). The reaction mixture was stirred at room temperature for two days then concentrated under vacuum. The crude material was purified by silica gel chromatography (50% to 67% ethyl acetate/hexane) to afford N-(4-chlorophenyl)-2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide (92 mg) as a white solid. MS (ESI, pos. ion) m/z: 428.1 (M+1).

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe crude material was purified by silica gel chromatography (50% to 67% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6b466a1c5ea54b34ae9f1c11291eb462
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

Loading…