Sodium Cyanide → HCID 90408243, compound

HRID 1855097Notes

Reaction equation

HRID 1855097 reaction equation
CS(O[CH2:6][CH2:7][C:8]12[CH2:15][CH2:14][C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:17]=3)([CH2:12][CH2:13]1)[CH2:10][O:9]2)(=O)=O.[C-:29]#[N:30].[Na+]>CS(C)=O.C(Cl)Cl>[O:22]([C:18]1[CH:17]=[C:16]([C:11]23[CH2:12][CH2:13][C:8]([CH2:7][CH2:6][C:29]#[N:30])([CH2:15][CH2:14]2)[O:9][CH2:10]3)[CH:21]=[CH:20][CH:19]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 90409802HCID 90409802, compound

Product 1

HCID 90408243HCID 90408243, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 110A compound (100 mg, 0.25 mmol) and NaCN (61 mg, 1.2 mmol) in DMSO (3 mL) was stirred at 80° C. overnight. The mixture was cooled to rt, diluted with DCM, washed with 1N aq HCl, dried (MgSO4), and concentrated in vacuo. The crude was chromatographed (SiO2; continuous gradient of hexanes/EtOAc from 100:0 to 50:50) to afford the title compound (62 mg, 75% yield) as a colorless oil. LCMS [M+H]+=334.3. 1H NMR (400 MHz, CDCl3) δ 7.38-7.32 (m, 2H), 7.31-7.25 (m, J=7.9, 7.9 Hz, 1H), 7.14-7.09 (m, 1H), 7.00 (dd, J=8.6, 1.1 Hz, 3H), 6.96 (t, J=2.0 Hz, 1H), 6.84 (ddd, J=8.1, 2.4, 0.9 Hz, 1H), 3.96 (s, 2H), 2.47-2.41 (m, 2H), 2.12-2.03 (m, 2H), 2.00-1.89 (m, 4H), 1.84-1.78 (m, 2H), 1.74-1.64 (m, 2H).

Workup

  1. temperatureThe mixture was cooled to rt
  2. washwashed with 1N aq HCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude was chromatographed (SiO2; continuous gradient of hexanes/EtOAc from 100:0 to 50:50)

Sources & evidence

ORD record
ord-36afbfbe190a424593cbc4b470ad1ee1
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

Loading…