HCID 57504888, compound → HCID 57504890, compound

HRID 2060757Notes

Reaction equation

HRID 2060757 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([C@:10]23[CH2:18][O:17][CH2:16][C@H:15]2[CH2:14][S:13][C:12]([NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:11]3)[CH:7]=[CH:8][CH:9]=1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C@:10]23[CH2:18][O:17][CH2:16][C@H:15]2[CH2:14][S:13][C:12]([NH:19][C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:11]3)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 57504888HCID 57504888, compound

Product 1

HCID 57504890HCID 57504890, compoundYield 18.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-((4aS,7aS)-7a-(3-azidophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide (0.62 g, 1.63 mmol) is diluted with ethanol (10 mL) and Pd on carbon (10%, wet, 0.062 g). The mixture is degassed and stirred at room temperature under hydrogen (30 psi) overnight. The mixture is filtered through diatomaceous earth using ethanol as a rinse. The solvent is removed under reduced pressure to give the title compound, (0.106 g, 18%). ES/MS m/e: 354 (M+1).

Workup

  1. customThe mixture is degassed
  2. filtrationThe mixture is filtered through diatomaceous earth
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-24b2debc193748759589999327f9e0d8
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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