Chloroacetonitrile → HCID 59259086, compound

HRID 641827Notes

Reaction equation

HRID 641827 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]#[CH:21])[CH:15]=[CH:14][C:13]=2[NH:22][CH2:23][C:24]2[NH:28][N:27]=[N:26][N:25]=2)=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:29]([O-:32])([O-])=[O:30].[K+].[K+].Cl[CH2:36][C:37]#N>CC(CC)=O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]#[CH:21])[CH:15]=[CH:14][C:13]=2[NH:22][CH2:23][C:24]2[N:25]=[N:26][N:27]([CH2:36][CH2:37][O:32][CH3:29])[N:28]=2)=[O:11])=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]#[CH:21])[CH:15]=[CH:14][C:13]=2[NH:22][CH2:23][C:24]2[N:28]([CH2:36][CH2:37][O:30][CH3:29])[N:27]=[N:26][N:25]=2)=[O:11])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 178458509HCID 178458509, compound

Product 2

HCID 59259086HCID 59259086, compoundHCID 86639829HCID 86639829, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1.04 g (2.77 mmol) (4-isopropyl-phenyl)-{5-prop-2-ynyloxy-2-[(1H-tetrazol-5-ylmethyl)-amino]-phenyl}-methanone, 0.85 g K2CO3, 0.25 g KI and 0.41 g (2.95 mmol) chloroacetonitrile and 40 ml ethyl methyl ketone is stirred at 60° C. for 20 h. The reaction mixture is cooled to room temperature and poured onto water and extracted with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane/EtOAc=2:1) to afford 0.65 g of (4-isopropyl-phenyl)-(2-{[2-(2-methoxy-ethyl)-2H-tetrazol-5-ylmethyl]-amino}-5-prop-2-ynyloxy-phenyl)-methanone (yellow oil, title compound) and 0.3 g of (4-isopropyl-phenyl)-(2-{[1-(2-methoxy-ethyl)-1H-tetrazol-5-ylmethyl]-amino}-5-prop-2-ynyloxy-phenyl)-methanone (yellow oil).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash-chromatography on silica gel (hexane/EtOAc=2:1)

Sources & evidence

ORD record
ord-25f4a9d594d548d09d1b6a10e80a622e
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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