1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57682700, compound

HRID 494226Notes

Reaction equation

HRID 494226 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[CH3:12])=[CH:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[C:22]([CH3:29])[N:21]=2)=[CH:16][CH:15]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:28]=[CH:27][C:23]([C:24]([NH:1][C:2]3[CH:11]=[C:10]4[C:5]([CH2:6][CH2:7][CH2:8][N:9]4[CH3:12])=[CH:4][CH:3]=3)=[O:25])=[C:22]([CH3:29])[N:21]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 112174211-Methyl-1,2,3,4-tetrahydroquinolin-7-amineHCID 242777906-(4-Fluorophenyl)-2-methylpyridine-3-carboxylic acid

Product 1

HCID 57682700HCID 57682700, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-amino-1-methyl-1,2,3,4-tetrahydroquinoline (D3) (31 mg, 0.19 mmol) in DCM (1 ml) was added 6-(4-fluorophenyl)-2-methylnicotinic acid (D24) (44 mg, 0.19 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (44 mg, 0.23 mmol) and 4-dimethylaminopyridine (11 mg, 0.09 mmol) and the reaction stirred at ambient temperature overnight. The crude reaction mixture was loaded directly onto a silica SPE column and eluted with 0-2% methanol/DCM to give the title compound as a solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.02 (dd, 2H), 7.84 (d, 1H), 7.57 (d, 1H), 7.35 (br, 1H), 7.17 (t, 2H), 7.00 (s, 1H), 6.93 (d, 1H), 6.74 (d, 1H), 3.25 (m, 2H), 2.93 (s, 3H), 2.80 (s, 3H), 2.74 (m, 2H), 1.96 (m, 2H)

Workup

  1. customThe crude reaction mixture
  2. washeluted with 0-2% methanol/DCM

Sources & evidence

ORD record
ord-4ef4c7387c464c2ebb3924ca6620d7d5
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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