Dicyclohexylcarbodiimide → HCID 68593446, compound

HRID 517860Notes

Reaction equation

HRID 517860 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.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32](O)=[O:33])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].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:32]([CH:29]3[CH2:30][CH2:31][N:26]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[CH2:27][CH2:28]3)=[O:33])[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 10868DicyclohexylcarbodiimideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 57876166HCID 57876166, compound

Product 1

HCID 68593446HCID 68593446, compoundYield 7.5%

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), 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (94 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 obtain 14 mg of tert-butyl 4-(2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethylcarbamoyl)piperidine-1-carboxylate 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). The compound obtained was taken in 3 ml of HCl in dioxane and stirred for 1 h to obtain 5 mg of N-(2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethyl)piperidine-4-carboxamide as HCl Salt. 1H NMR (DMSO) 10.78 (bs, 1H), 8.1 (bs, 1H), 7.40 (d, 1H), 7.2 (s, 1H), 7.05 (d, 1H), 4.6-4.2 (m, 1H), 4.3-4.2 (m, 1H), 4.2 (m, 2H), 4.0-3.8 (m, 3H), 3.35-3.05 (m, 4H), 3.0 (s, 3H), 2.95-2.8 (m, 2H), 2.4 (s, 3H), 2.3-2.2 (m, 1H), 2.1-2.00 (m, 1H), 1.8-1.6 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-6647659811ec4d9790eb08ae27634d7c
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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