Tributyltin azide → HCID 178454218, compound

HRID 574261Notes

Reaction equation

HRID 574261 reaction equation
[C:1]([O:5][C:6](=[O:51])[NH:7][C@H:8]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=3)[CH2:19][CH2:18]2)=[CH:13][N:12]([CH2:32][C:33]2[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[CH:35][C:34]=2[F:43])[C:11]1=[O:44])([CH3:4])([CH3:3])[CH3:2].[N:52]([Sn](CCCC)(CCCC)CCCC)=[N+:53]=[N-:54]>C1(C)C=CC=CC=1.ClCCl>[C:1]([O:5][C:6](=[O:51])[NH:7][C@H:8]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]4[NH:54][N:53]=[N:52][N:31]=4)[CH:25]=3)[CH2:19][CH2:18]2)=[CH:13][N:12]([CH2:32][C:33]2[C:38]([C:39]([F:40])([F:41])[F:42])=[CH:37][CH:36]=[CH:35][C:34]=2[F:43])[C:11]1=[O:44])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4984872Tributyltin azide2×HCID 67144622HCID 67144622, compound

Product 1

HCID 178454218HCID 178454218, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

{(R)-2-[5-[4-(3-cyano-benzyl)-piperazin-1-yl]-3-(2-fluoro-6-trifluoromethyl-benzyl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (35 mg, 0.049 mmol), and azidotributyl tin (IV) (16 μl, 0.059 mmol) were dissolved at 120° C. for 10 hrs in toluene (1 mL) with stirring. The solution was cooled to room temperature, followed by the addition of azidotributyl tin (IV) (20 μl, 0.074 mmol) thereto and stirring at 120° C. for an additional 2 hrs. The solution was cooled to room temperature, diluted in dichloromethane, and washed with an aqueous saturated ammonium chloride solution and an aqueous saturated sodium chloride solution in the order. The organic layer thus formed was separated and concentrated, and the residue was purified using silica gel chromatography (eluent: dichloromethane/methanol, 6/1) and dried in a vacuum to afford 20 mg of the compound as a colorless oil (yield 54%).

Workup

  1. stirringstirring at 120° C. for an additional 2 hrs
  2. temperatureThe solution was cooled to room temperature
  3. washwashed with an aqueous saturated ammonium chloride solution
  4. customThe organic layer thus formed
  5. customwas separated
  6. concentrationconcentrated
  7. customthe residue was purified
  8. customdried in a vacuum

Sources & evidence

ORD record
ord-96daa9c3cfb54d3fa32a55d4ea3e6d01
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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