Dibutyltin oxide → HCID 59768614, compound

HRID 2217907Notes

Reaction equation

HRID 2217907 reaction equation
[Cl:1][C:2]1[C:3]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][C:20]#[N:21])[CH2:13]1)[CH:6]=[CH:5]2.C[Si]([N:36]=[N+:37]=[N-:38])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][C:20]3[N:36]=[N:37][NH:38][N:21]=3)[CH2:13]1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 68809044HCID 68809044, compound

Product 1

HCID 59768614HCID 59768614, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[6-Chloro-2-[(3S)-3-[(2-cyanoethyl)amino]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (example 87 (b)) (0.15 g), trimethylsilylazide (0.091 ml), dibutyltin oxide (0.009 g) and toluene (5 ml) were heated within a single mode microwave in a sealed 10 ml vial at 100° C. for 30 minutes and then at 120° C. for 120 minutes. The reaction was cooled to room temperature, filtered and washed with toluene. The solid was then triturated with methanol and filtered before being dissolved in hot methanol and purified by Varian SCX cartridge (methanol (50 ml) and then ammonia in methanol (0.7M, 50 ml) as eluant). to afford the title compound (0.025 g).

Workup

  1. customwere heated within a single mode microwave in a sealed 10 ml vial at 100° C. for 30 minutes
  2. filtrationfiltered
  3. washwashed with toluene
  4. customThe solid was then triturated with methanol
  5. filtrationfiltered
  6. dissolutionbefore being dissolved in hot methanol
  7. custompurified by Varian SCX cartridge (methanol (50 ml)

Sources & evidence

ORD record
ord-837091b3e8de4861bc887cc38f16f817
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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