Isobutyric Acid → HCID 44160056, compound

HRID 517856Notes

Reaction equation

HRID 517856 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)(=[O:23])[CH:20]([CH3:22])[CH3:21].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:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[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 6590Isobutyric AcidHCID 10868DicyclohexylcarbodiimideHCID 57876166HCID 57876166, compound

Product 1

HCID 44160056HCID 44160056, compoundYield 12.4%

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, 0.411 mmol), isobutyric acid (36 mg, 0.411 mmol), N,N′-dicyclohexylcarbodiimide (93 mg, 0.452 mmol) and 4-dimethylaminopyridine (55 mg, 0.452 mmol) in dry dichloromethane (5.0 ml) were stirred at room temperature for 4 h. The reaction mixture was filtered through Celite and concentrated using rotary evaporator to afford 16 mg of N-(2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)ethyl)isobutyramide 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) 9.95 (bs, 1H), 7.9 (t, 1H), 7.4 (d 1H), 7.2 (s, 1H), 7.0 (d, 1H), 4.5-4.61 (m, 1H), 4.1-4.28 (m, 3H), 3.7-3.9 (m, 2H), 3.1-3.2 (m, 2H), 2.95 (s, 3H), 2.4 (s, 3H), 2.19-2.3 (m, 1H), 1.2-1.38 (m, 2H), 0.9 (d, 6H).

Workup

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

Sources & evidence

ORD record
ord-77ca94159a544c15b58b01b077136139
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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