Cyclohexanecarboxylic acid → HCID 44160057, compound

HRID 517857Notes

Reaction equation

HRID 517857 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.[CH:19]1([C:25](O)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][N:2]1[CH2:18][CH2:17][C:5]2[N:6]([CH2:14][CH2:15][NH:16][C:25]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:26])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

6

Reactant 3

HCID 7413Cyclohexanecarboxylic acidHCID 10868DicyclohexylcarbodiimideHCID 57876166HCID 57876166, compound

Product 1

HCID 44160057HCID 44160057, compoundYield 6.9%

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), cyclohexane carboxylic acid (52 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 using rotary evaporator to afford 10 mg of N-(2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethyl)cyclohexanecarboxamide as TFA salt after purification by reversed-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) 9.94 (bs, 1H), 7.86 (t, 1H), 7.38 (d, 1H), 7.11 (s, 1H), 7.0 (d, 1H), 4.56-4.63 (m, 1H), 4.22-4.29 (m, 1H), 4.08-4.13 (m, 3H), 3.72-3.81 (m, 3H), 3.08-3.14 (m, 3H), 2.97 (s, 3H), 2.38 (s, 3H), 1.95-2.0 (m, 1H), 1.50-1.84 (m, 5H), 1.02-1.2 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. customevaporator

Sources & evidence

ORD record
ord-78395853082e4ce9ab64e0efd0e69b35
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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