Azido(trimethyl)stannane → HCID 178521683, compound

HRID 1424605Notes

Reaction equation

HRID 1424605 reaction equation
[C:1]([CH2:3][CH:4]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:6]2([CH2:11][CH2:10][N:9]([C:12]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:13])[CH2:8][CH2:7]2)[CH2:5]1)#[N:2].[Sn]([N:31]=[N+:32]=[N-:33])(C)(C)C>C1(C)C=CC=CC=1>[NH:31]1[C:1]([CH2:3][CH:4]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:6]3([CH2:11][CH2:10][N:9]([C:12]([NH:14][CH:15]4[CH:20]5[CH2:26][CH:4]6[CH2:5][CH:18]([CH2:17][CH:16]4[CH2:3]6)[CH2:19]5)=[O:13])[CH2:8][CH2:7]3)[CH2:5]2)=[N:2][N:33]=[N:32]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 66953299HCID 66953299, compound

Product 1

HCID 178521683HCID 178521683, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (±)-3-(cyanomethyl)-N-cyclohexyl-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxamide (30 mg, 0.075 mmol) in toluene (2 mL), Me3SnN3 (80 mg, 0.375 mmol) was added. The reaction mixture was stirred at 80° C. overnight. The mixture was concentrated. The crude product was purified by preparative HPLC to afford (±)-3-((1H-tetrazol-5-yl)methyl)-N-(2-adamantyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxamide (15 mg, 45%). LC-MS Method 5 tR=1.28 min, m/z=447.3; 1H NMR (CD3OD): δ=1.62-1.69 (m, 2H), 1.71-1.86 (m, 4H), 1.89-2.24 (m, 13H), 2.56-2.68 (m, 1H), 3.09-3.29 (m, 3H), 3.49 (s, 1H), 3.66-3.74 (m, 1H), 3.1-3.90 (m, 1H), 3.99 (s, 1H), 4.09-4.21 (m, 2H), 7.27 (d, 1H), 7.30-7.49 (m, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-8fa8b64bbc39432ebd7138f9b25b10b5
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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