1-Pyrrolidineethanamine → HCID 86732822, compound

HRID 525953Notes

Reaction equation

HRID 525953 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[C:11]=2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:6](=[O:33])[C:5]([C:34](O)=[O:35])=[CH:4]1)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[N:70]1([CH2:75][CH2:76][NH2:77])[CH2:74][CH2:73][CH2:72][CH2:71]1>CN(C)C=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[C:11]=2[O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:6](=[O:33])[C:5]([C:34]([NH:77][CH2:76][CH2:75][N:70]2[CH2:74][CH2:73][CH2:72][CH2:71]2)=[O:35])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 13441-PyrrolidineethanamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86732819HCID 86732819, compound

Product 1

HCID 86732822HCID 86732822, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-ethyl-7,8-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (Example 44f) (7 g, 14.30 mmol) in N,N-Dimethylformamide (DMF) (50 mL) was added HATU (8.16 g, 21.45 mmol) and DIPEA (7.49 mL, 42.9 mmol), the resulting mixture was stirred at r.t. for 30 min. 2-(Pyrrolidin-1-yl)ethanamine (2.70 mL, 21.45 mmol) was added and the resulting mixture was stirred at r.t. for 3 h. The mixture was concentrated and the residue was purified by normal phase automatic silica column chromatography (Combiflash RF), eluting with MeOH/DCM (0-30%) to afford 1-ethyl-7,8-bis((4-methoxybenzyl)oxy)-4-oxo-N-(2-(pyrrolidin-1-yl)ethyl)-1,4-dihydroquinoline-3-carboxamide (6.6 g, 11.27 mmol, 79% yield) as a pale yellow solid. LCMS: (M+H)+: 586.5.

Workup

  1. stirringthe resulting mixture was stirred at r.t. for 3 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by normal phase automatic silica column chromatography (Combiflash RF)
  4. washeluting with MeOH/DCM (0-30%)

Sources & evidence

ORD record
ord-ca8d2e1ca46442b7a12ab458d50c782d
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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