Stannous Chloride → HCID 89761691, compound

HRID 528557Notes

Reaction equation

HRID 528557 reaction equation
[CH3:1][O:2][C:3]1[CH:50]=[CH:49][C:6]([CH2:7][N:8]([C:44]2[S:45][CH:46]=[CH:47][N:48]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:21]4[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:22]=4[C:30]4[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH:31]=4)[CH2:19][CH2:18][O:17][C:16]=3[CH:43]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[Sn](Cl)Cl>CO>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([N:20]2[CH2:19][CH2:18][O:17][C:16]3[CH:43]=[C:12]([S:9](=[O:10])(=[O:11])[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:50][CH:49]=4)[C:44]4[S:45][CH:46]=[CH:47][N:48]=4)[CH:13]=[CH:14][C:15]2=3)=[C:22]([C:30]2[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])[CH2:32][CH:31]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 89761707HCID 89761707, compound

Product 1

HCID 89761691HCID 89761691, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)-5-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (0.159 g, 0.221 mmol) in methanol (1.104 mL) was added tin(II) chloride (0.168 g, 0.884 mmol) and the reaction was stirred at RT for 1 h. The reaction was then heated to 60° C. for 1.5 h. The reaction mixture was concentrated under a vacuum. The residue was taken up in EtOAc, and washed with 1N NaOH (to a pH that is basic) and the layers were separated. The organic layer was washed with brine and dried over magnesium sulfate, filtered, and concentrated under a vacuum. The material was dissolved in methanol and purified via 2 g SCX column to provide tert-butyl 4-(5-amino-2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate, which was taken forward without further purification. m/z (ESI) 690.2 (M+H)+.

Workup

  1. temperatureThe reaction was then heated to 60° C. for 1.5 h
  2. concentrationThe reaction mixture was concentrated under a vacuum
  3. washwashed with 1N NaOH (to a pH that
  4. customwere separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under a vacuum
  9. dissolutionThe material was dissolved in methanol
  10. custompurified via 2 g SCX column

Sources & evidence

ORD record
ord-bbb61eea4c6f4fabbed60470629c5e7a
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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