4-Chloroaniline → HCID 24958099, compound

HRID 2196584Notes

Reaction equation

HRID 2196584 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:17][CH2:16][C:15]3[C:14]([C:18]([O-:20])=O)=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9]2)=[CH:3][CH:2]=1.[Na+].[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:18]([C:14]2[C:15]3[CH2:16][CH2:17][N:8]([CH2:7][C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)[CH2:9][C:10]=3[CH:11]=[CH:12][CH:13]=2)=[O:20])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69047155HCID 69047155, compound

Product 1

HCID 24958099HCID 24958099, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium 2-(pyridin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate (80 mg, 0.276 mmol) was dissolved in N,N-dimethylformamide (1 mL) then added 4-chloroaniline (42 mg, 0.331 mmol), 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (133 mg, 0.414 mmol), and N,N-diisopropylethylamine (56 mg, 0.552 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum. The remaining orange oil was purified by silica gel chromatography (1% to 3% 7N ammonia in methanol/dichloromethane) to afford N-(4-chlorophenyl)-2-(pyridin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide (89 mg) as a light yellow solid. MS (ESI, pos. ion) m/z: 378.0 (M+1).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customThe remaining orange oil was purified by silica gel chromatography (1% to 3% 7N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-b1e814995ee648ea95f85c2c4870c952
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

Loading…