1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N,N-dimethyl-N-{4-oxo4-[5-(5-vinyl-3H-imidazo[4,5-b]pyridin-3-yl)-2,3-dihydro-1H-indol-1-yl]butyl}amine

HRID 1175736Notes

Reaction equation

HRID 1175736 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][C:16]([CH:19]=[CH2:20])=[CH:17][CH:18]=[C:13]4[N:12]=[CH:11]3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl.[CH3:22][N:23]([CH3:30])[CH2:24][CH2:25][CH2:26][C:27](O)=[O:28].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:22][N:23]([CH3:30])[CH2:24][CH2:25][CH2:26][C:27](=[O:28])[N:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:14]4=[N:15][C:16]([CH:19]=[CH2:20])=[CH:17][CH:18]=[C:13]4[N:12]=[CH:11]3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 126916404-(Dimethylamino)butyric acid hydrochlorideHCID 595597143-(2,3-dihydro-1H-indol-5-yl)-5-vinyl-3H-imidazo[4,5-b]pyridine2×

Product 1

HCID 59559704N,N-dimethyl-N-{4-oxo4-[5-(5-vinyl-3H-imidazo[4,5-b]pyridin-3-yl)-2,3-dihydro-1H-indol-1-yl]butyl}amine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)-5-vinyl-3H-imidazo[4,5-b]pyridine (48.0 mg, 0.14 mmol) (Intermediate 10.1), 4-(dimethylamino)butyric acid hydrochloride (36.3 mg, 0.21 mmol), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (54.9 mg, 0.29 mmol), 4-dimethylaminopyridine (122.5 mg, 1.00 mmol), and dichloromethane (8 ml) is stirred for 24 h at ambient temperature. The mixture is successively extracted with saturated aqueous ammonium chloride and saturated aqueous sodium bicarbonate. The organic layer is dried over sodium sulfate and concentrated in vacuo to render 50.4 mg (94%) of the respective amide. HPLC (over 10 min 10-85% MeCN/100 mM aq. NaOAc): 92% purity, tR 6.27 min (tR(SM) 6.61 min).

Workup

  1. extractionThe mixture is successively extracted with saturated aqueous ammonium chloride and saturated aqueous sodium bicarbonate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customHPLC (over 10 min 10-85% MeCN/100 mM aq. NaOAc)
  5. custom92% purity, tR 6.27 min (tR(SM) 6.61 min)

Sources & evidence

ORD record
ord-a8ce7b5063b747ec954fd0abd0a2747f
Source dataset
uspto-grants-2010_11
Patent number
US07842698B2

Reaction notes

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