Azido(trimethyl)stannane → HCID 178461654, compound

HRID 2037538Notes

Reaction equation

HRID 2037538 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@:20]([CH2:30][CH2:31][C:32]#[N:33])([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18]2=[O:34])[CH3:16])=[CH:11][CH:10]=1.[Sn]([N:39]=[N+:40]=[N-:41])(C)(C)C>C1(C)C=CC=CC=1>[NH:39]1[C:32]([CH2:31][CH2:30][C@@:20]2([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:19][C:18](=[O:34])[N:17]([C@H:15]([C:12]3[CH:13]=[CH:14][C:9]([C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[F:1])=[CH:10][CH:11]=3)[CH3:16])[CH2:22][CH2:21]2)=[N:33][N:41]=[N:40]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 58109410HCID 58109410, compound

Product 1

HCID 178461654HCID 178461654, compoundYield 22.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-((R)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanenitrile (40 mg, 0.086 mmol) in anhydrous toluene (3 mL) was added Me3SnN3 (89 mg, 0.43 mmol) at 0° C. The mixture was refluxed overnight. The solvent was removed under reduced pressure and the residue was purified by preparative TLC to afford (R)-6-(2-(1H-tetrazol-5-yl)ethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (10 mg, yield: 22%). 1H NMR (CDCl3): 1.20 (m, 3H), 1.73-1.88 (m, 1H), 1.91-2.07 (m, 4H), 2.20-2.31 (m, 1H), 2.58-2.77 (m, 2H), 5.43 (m, 1H), 6.67-6.90 (m, 7H), 7.01 (m, 2H), 7.11 (m, 2H), 7.18 (m, 1H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-7dbb7a19937b4ef6b0bb613acf0d07d9
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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