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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(5-Chloroquinolin-7-yl)-6-(4-Fluorophenyl)-2-ethyl-nicotinamide

HRID 494277
Notes
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Reaction equation

HRID 494277 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([Cl:12])[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]([OH:26])=O)=[C:22]([CH3:29])[N:21]=2)=[CH:16][CH:15]=1.Cl.[CH3:31]N(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:12][C:4]1[CH:3]=[C:2]([NH:1][C:24](=[O:26])[C:23]2[CH:27]=[CH:28][C:20]([C:17]3[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=3)=[N:21][C:22]=2[CH2:29][CH3:31])[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 242777906-(4-Fluorophenyl)-2-methylpyridine-3-carboxylic acidHCID 690423405-Chloroquinolin-7-amine

Product 1

HCID 86760866N-(5-Chloroquinolin-7-yl)-6-(4-Fluorophenyl)-2-ethyl-nicotinamide

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-amino-5-chloroquinoline (D83) (50 mg, 0.28 mmol) in DCM (3 ml) was added 6-(4-fluorophenyl)-2-methyl-nicotinic acid (D24) (30 mg, 0.13 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (59 mg, 0.31 mmol) and 4-dimethylaminopyridine (17 mg, 0.14 mmol) and the reaction stirred at room temperature then at reflux until complete by tlc. The mixture was washed with sat. aq. sodium bicarbonate solution then dried over MgSO4 and concentrated to give the crude product. Purification by SPE column chromatography gave the title compound as an off white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.94 (dd, 1H), 8.54 (d, 1H), 8.29 (s, 1H), 8.05 (m, 3H), 7.92 (d, 1H), 7.78 (br.s, 1H), 7.62 (d, 1H), 7.47 (dd, 1H), 7.18 (t, 2H), 2.84 (s, 3H).

Workup

  1. temperatureat reflux until complete by tlc
  2. washThe mixture was washed with sat. aq. sodium bicarbonate solution
  3. dry with materialthen dried over MgSO4
  4. concentrationconcentrated
  5. customto give the crude product
  6. customPurification by SPE column chromatography

Sources & evidence

ORD record
ord-3683c93bc55f416698da9a4ce408167f
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538121B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes