Azido(trimethyl)stannane → HCID 178436413, compound

HRID 2099750Notes

Reaction equation

HRID 2099750 reaction equation
[C:1]([CH:3]([NH:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[NH:28][C:27]2=[O:36])[CH2:22][CH2:21]1)=[O:19])[CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([CH2:14][CH3:15])[CH:13]=1)[NH:10][N:9]=[C:8]2[CH3:16])#[N:2].[N:37]([Sn](C)(C)C)=[N+:38]=[N-:39]>O1CCCC1>[CH2:14]([C:12]1[CH:13]=[C:5]([CH2:4][CH:3]([NH:17][C:18]([N:20]2[CH2:21][CH2:22][CH:23]([N:26]3[CH2:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[NH:28][C:27]3=[O:36])[CH2:24][CH2:25]2)=[O:19])[C:1]2[NH:39][N:38]=[N:37][N:2]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[C:8]2[CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 178436302HCID 178436302, compound

Product 1

HCID 178436413HCID 178436413, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carboxylic acid [1-cyano-2-(7-ethyl-3-methyl-1H-indazol-5-yl)-ethyl]-amide (0.25 g, 0.5 mmol) in tetrahydrofuran (6 mL) was treated with azidotrimethyltin (0.16 g, 0.77 mmol). The resulting suspension was heated at reflux overnight. The solvents were evaporated, dissolved in ethyl acetate and washed with water (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography afforded the desired tetrazole. 1H-NMR (CD3OD) δ 1.3 (t, J=7.6, 3H), 1.45-1.70 (m, 4H), 1.87 (m, 1H), 2.0 (s, 3H), 2.75-2.90 (m, 4H), 3.42 (m, 1H), 3.72 (d, J=6.6, 1H), 4.12 (m, 4H), 4.88 (m, 1H), 5.48 (dd, J=7.0, 7.9, 1H), 6.77 (d, J=7.9, 1H), 6.94 (m, 1H) 6.98 (s, 1H), 7.09 (d, J=7.3, 1H), 7.14 (dd, J=7.9, 7.6, 1H), 7.30 (s, 1H). Mass spec.: 529.26 (MH)+.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux overnight
  3. customThe solvents were evaporated
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with water (2×), brine (2×)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4415ad3c60ca4faa9c33871235ab9506
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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