N-(3-Aminopropyl)morpholine → HCID 9804918, compound

HRID 986995Notes

Reaction equation

HRID 986995 reaction equation
ON1C2C=CC=CC=2N=N1.[NH2:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.Cl.CN(C)CCCN=C=NCC.[Cl:33][C:34]1[CH:55]=[CH:54][C:37]([O:38][C:39]2[C:48]3[C:43](=[CH:44][C:45]([O:52][CH3:53])=[C:46]([C:49](O)=[O:50])[CH:47]=3)[N:42]=[CH:41][CH:40]=2)=[C:36]([F:56])[CH:35]=1>CN(C=O)C.O.C(N(CC)CC)C>[Cl:33][C:34]1[CH:55]=[CH:54][C:37]([O:38][C:39]2[C:48]3[C:43](=[CH:44][C:45]([O:52][CH3:53])=[C:46]([C:49]([NH:11][CH2:12][CH2:13][CH2:14][N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[O:50])[CH:47]=3)[N:42]=[CH:41][CH:40]=2)=[C:36]([F:56])[CH:35]=1

Participants

8

Reactant 4

HCID 61055N-(3-Aminopropyl)morpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11268045HCID 11268045, compound

Product 1

HCID 9804918HCID 9804918, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

N-Hydroxybenzotriazole (0.104 g), triethylamine (0.095 ml), N-(3-aminopropyl)morpholine (0.11 ml) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.142 g) were added in turn to a stirred mixture of 4-(4-chloro-2-fluorophenoxy)-7-methoxyquinoline-6-carboxylic acid (0.2 g) in DMF (5 ml). The reaction mixture was stirred at ambient temperature for 16 hours. Water (20 ml) was added and the resultant suspension was transferred onto a C18 reversed-phase silica gel chromatography column and eluted with a decreasingly polar solvent gradient of water and acetonitrile. There was thus obtained the title compound (0.175 g); NMR Spectrum: (DMSOd6) 1.72 (m, 2H), 2.38 (m, 6H), 3.35 (m, 2H), 3.56 (m, 4H), 4.01 (s, 3H), 6.56 (d, 1H), 7.42-7.59 (m, 3H), 7.76 (m, 1H), 8.38 (m, 1H), 8.51 (s, 1H), 8.68 (d, 1H); Mass Spectrum: M+H+ 474 & 476.

Workup

  1. washeluted with a decreasingly polar solvent gradient of water and acetonitrile

Sources & evidence

ORD record
ord-7570439b5f9648edba3e575a1ca41202
Source dataset
uspto-grants-2003_10
Patent number
US06630489B1

Reaction notes

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