Chloroacetonitrile → HCID 59259086, compound

HRID 1046362Notes

Reaction equation

HRID 1046362 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-56945d1764ea4de696ad678266f8681b
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

Loading…