Triethylamine → HCID 25254917, compound

HRID 444759Notes

Reaction equation

HRID 444759 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.[N:25]1([CH2:30][CH2:31][CH2:32][NH2:33])[CH:29]=[N:28][CH:27]=[N:26]1.C(N(CC)CC)C>CS(C)=O>[N:25]1([CH2:30][CH2:31][CH2:32][NH:33][C:10]2[C:9]3[O:14][CH2:15][C:16]4([CH2:17][CH2:18][CH2:19][CH2:20]4)[N:7]4[C:8]=3[C:3]([C:4](=[O:24])[C:5]([C:21]([OH:23])=[O:22])=[CH:6]4)=[C:2]([NH2:1])[C:11]=2[F:12])[CH:29]=[N:28][CH:27]=[N:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 43796821H-1,2,4-Triazole-1-propanamineHCID 58134647HCID 58134647, compound

Product 1

HCID 25254917HCID 25254917, compoundYield 18.1%

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 3-(1H-1,2,4-triazol-1-yl)propan-1-amine (5 mg, 0.04 mmol) and 5.5 μL triethylamine in DMSO (0.3 mL) was stirred at 90° C. for 24 h. The reaction mixture was cooled and freeze-dried overnight. The crude product was taken up in ACN and purified by prep HPLC to yield 10-(3-(1H-1,2,4-triazol-1-yl)propylamino)-8-amino-9-fluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1′-cyclopentane]-6-carboxylic acid (3.2 mg, 18%) as a yellow solid. MS (EP) m/z: 443 (M++1). (Calcd. For C21H23FN6O4, 442.18).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customfreeze-dried overnight
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-daecb24c112c4db4bc8986f7259cc4c3
Source dataset
uspto-grants-2013_07
Patent number
US08476261B2

Reaction notes

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