Trityl chloride → HCID 22479975, compound

HRID 1353766Notes

Reaction equation

HRID 1353766 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[N:10]=[C:9]2[Br:21].[C:22]1([C:28](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>CN(C)C=O>[Br:21][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([C:5]3[N:4]=[N:3][N:2]([C:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[N:1]=3)[CH:7]=2)[N:11]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:10]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 69421917HCID 69421917, compound

Product 1

HCID 22479975HCID 22479975, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(5-(2H-1,2,3,4-tetrazol-5-yl)-3-bromo-1H-indazolyl)perhydro-2H-pyran (0.554 g 1.59 mmol) in dimethyl formamide (5 mL) was added triphenylmethyl chloride (0.662 g, 2.38 mmol), and triethyl amine (1.110 mL, 7.95 mmol). The reaction was heated to reflux temperature for 3.5 hours and maintained at room temperature overnight. The solvent was removed under reduced pressure. The resulting solid was dissolved in 20 mL of ethyl acetate was washed with 10 ml-portions of water. The title compound was purified by column chromatography (SiO2, 20% ethyl acetate in hexanes) (0.74 g, 70%): ES-MS (m/z) mass not detected.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux temperature for 3.5 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe resulting solid was dissolved in 20 mL of ethyl acetate
  5. washwas washed with 10 ml-portions of water
  6. customThe title compound was purified by column chromatography (SiO2, 20% ethyl acetate in hexanes) (0.74 g, 70%)

Sources & evidence

ORD record
ord-447f7d8216024cd1b6b99e7f2578366b
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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