Dicyclohexylcarbodiimide → HCID 44160058, compound

HRID 517858Notes

Reaction equation

HRID 517858 reaction equation
[CH3:1][N:2]1[CH2:18][CH2:17][C:5]2[N:6]([CH2:14][CH2:15][NH2:16])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[Cl:19][C:20]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:21]=1[C:22](O)=[O:23].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[Cl:19][C:20]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:21]=1[C:22]([NH:16][CH2:15][CH2:14][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=2[C:4]2[CH2:3][N:2]([CH3:1])[CH2:18][CH2:17][C:5]1=2)=[O:23]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 752592-Chloro-4-fluorobenzoic acidHCID 57876166HCID 57876166, compound

Product 1

HCID 44160058HCID 44160058, compoundYield 1.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethanamine (100 mg, 0.41 mmol), 2-chloro 4-fluoro benzoic acid (71.8 mg, 0.41 mmol), N,N′-dicyclohexylcarbodiimide (93 mg, 0.45 mmol) and 4-dimethylaminopyridine (55.22 mg, 0.45 mmol) in dry dichloromethane (2.5 ml) were stirred at room temperature for 3 h. The reaction mixture was filtered through Celite and concentrated by rotary evaporation to obtain 2.93 mg of 2-chloro-4-fluoro-N-(2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethyl)benzamide as TFA salt after purification by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 0.5 ml). 1H NMR (DMSO) 10.0 (bs, 1H), 8.6 (t, 1H), 7.5 (d, 1H), 7.4 (d, 1H), 7.1-7.25 (m, 3H), 7.0 (d, 1H), 4.55-4.60 (m, 1H), 4.15-4.35 (m, 4H), 3.70-3.8 (m, 2H), 3.09-3.2 (m, 3H), 2.95 (s, 3H), 2.4 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-b5ab74cda63340a29cf5ba6152123bbd
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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