Triethylamine → HCID 25254916, compound

HRID 444758Notes

Reaction equation

HRID 444758 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]2[O:14][CH2:15][C:16]3([CH2:20][CH2:19][CH2:18][CH2:17]3)[N:7]3[C:8]=2[C:3]=1[C:4](=[O:24])[C:5]([C:21]([OH:23])=[O:22])=[CH:6]3.[CH3:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[C:28]([NH:36][CH2:37][CH2:38][NH2:39])[CH:27]=1.C(N(CC)CC)C>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:39][CH2:38][CH2:37][NH:36][C:28]2[CH:27]=[C:26]([CH3:25])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]=2)[C:9]2[O:14][CH2:15][C:16]3([CH2:17][CH2:18][CH2:19][CH2:20]3)[N:7]3[C:8]=2[C:3]=1[C:4](=[O:24])[C:5]([C:21]([OH:23])=[O:22])=[CH:6]3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1847837N1-(4-methylquinolin-2-yl)ethane-1,2-diamineHCID 58134647HCID 58134647, compound

Product 1

HCID 25254916HCID 25254916, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 8-amino-9,10-difluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]-quinoline-3,1′-cyclopentane]-6-carboxylic acid (13 mg, 0.04 mmol) and N1-(4-methylquinolin-2-yl)ethane-1,2-diamine (10 mg, 0.05 mmol) and 11 μL triethylamine in DMSO (0.3 mL) was stirred at 90° C. for 72 h. The reaction mixture was cooled and freeze-dried overnight. The crude product was taken up in CH2Cl2 and purified by preparative TLC to yield 8-amino-9-fluoro-10-(2-(4-methylquinolin-2-ylamino)ethylamino)-7-oxo-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1′-cyclopentane]-6-carboxylic acid (0.8 mg, 4%) as a yellow solid. MS (EP) m/z: 518 (M++1). (Calcd. for C28H28FN5O4, 517.21).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customfreeze-dried overnight
  3. custompurified by preparative TLC

Sources & evidence

ORD record
ord-aeea485d6ba94f51a0348894792a95d8
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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