4-Fluorobenzoic Acid → HCID 44160180, compound

HRID 517861Notes

Reaction equation

HRID 517861 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.[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:16][CH2:15][CH2:14][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]3[CH2:3][N:2]([CH3:1])[CH2:18][CH2:17][C:5]2=3)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 99734-Fluorobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 57876166HCID 57876166, compound

Product 1

HCID 44160180HCID 44160180, compoundYield 12.8%

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 (0.1 g, 0.41 mmol), 4-fluoro benzoic acid (57 mg, 0.41 mmol), N,N′-dicyclohexylcarbodiimide (93 mg, 0.45 mmol) and 4-dimethylaminopyridine (55 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 19.22 mg of 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. 5 ml). 1H NMR (DMSO) 9.98 (bs, 1H), 8.72 (t, 1H), 7.80-7.84 (m, 2H), 7.45 (d, 1H), 7.25-7.30 (m, 2H), 7.20 (s, 1H), 7.0 (d, 1H), 4.50-4.59 (m, 1H), 4.17-4.30 (m, 2H), 3.73-3.80 (m, 2H), (3.50-3.59 (m, 3H), 3.05-3.15 (m, 2H), 2.92 (s, 3H), 2.37 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-1a4c1aafe8144f228525ca2c224bb94f
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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