Water → 8-Amino-9-fluoro-7-oxo-10-(3-(pyridin-2-yl)propylamino)-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1'-cyclopropane]-6-carbonitrile

HRID 1396123Notes

Reaction equation

HRID 1396123 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]2[O:14][CH2:15][C:16]3([CH2:18][CH2:17]3)[N:7]3[C:8]=2[C:3]=1[C:4](=[O:21])[C:5]([C:19]#[N:20])=[CH:6]3.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][CH2:30][NH2:31].C(N(CC)CC)C.O>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:31][CH2:30][CH2:29][CH2:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=2)[C:9]2[O:14][CH2:15][C:16]3([CH2:18][CH2:17]3)[N:7]3[C:8]=2[C:3]=1[C:4](=[O:21])[C:5]([C:19]#[N:20])=[CH:6]3

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31596143-(Pyridin-2-yl)propan-1-amineHCID 581346818-Amino-9,10-difluoro-7-oxo-2,7-dihydrospiro[[1,4]oxazino-[2,3,4-ij]quinoline-3,1'-cyclopropane]-6-carbonitrile

Product 1

HCID 252527558-Amino-9-fluoro-7-oxo-10-(3-(pyridin-2-yl)propylamino)-2,7-dihydrospiro[[1,4]oxazino[2,3,4-ij]quinoline-3,1'-cyclopropane]-6-carbonitrileYield 17.2%

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′-cyclopropane]-6-carbonitrile (320 mg, 1.1 mmol) and 3-(pyridine-2-yl)propan-1-amine (270 mg, 2 mmol) and triethylamine (221 μL, 2.7 mmol) in DMSO (8 mL) was stirred at 120° C. for 15 hr. The reaction mixture was added portion wise to water and was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The dry residue was purified by column chromatograph (ethylacetate, to ethylacetate-MeOH 10:1) to yield the title compound (76.9 mg) as a yellow solid. MS (EP) m/z: 406.2 (M++1). (Calcd for C22H20FN5O2, 405.42). 1H NMR (400 MHz, CD3OD) δ 1.15 (2H, t), 1.59 (2H, t), 2.03 (2H, t), 2.88 (2H, t), 3.54 (2H, m), 4.15 (2H, s), 7.23 (1H, m), 7.33 (1H, m), 7.74 (1H, m), 8.04 (1H, s), 8.42 (1H, m)

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe dry residue was purified by column chromatograph (ethylacetate, to ethylacetate-MeOH 10:1)

Sources & evidence

ORD record
ord-c7530bed656c4d4d8ff8ed43572a7c96
Source dataset
uspto-grants-2014_12
Patent number
US08901112B2

Reaction notes

Loading…