Ethyl isocyanate → HCID 9936069, compound

HRID 1374116Notes

Reaction equation

HRID 1374116 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[O:17][CH:18]([C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=1)[CH2:19][CH2:20][CH2:21][N:22]1[CH2:29][CH:28]2[O:30][CH:24]([CH2:25][NH:26][CH2:27]2)[CH2:23]1>CC#N.C(Cl)(Cl)Cl>[C:35]([C:34]1[CH:33]=[CH:32][C:31]([CH:18]([O:17][C:16]2[CH:39]=[CH:40][C:41]([O:42][CH3:43])=[C:14]([O:13][CH3:12])[CH:15]=2)[CH2:19][CH2:20][CH2:21][N:22]2[CH2:29][CH:28]3[O:30][CH:24]([CH2:25][N:26]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])[CH2:27]3)[CH2:23]2)=[CH:38][CH:37]=1)#[N:36]

Participants

6

Reactant 3

HCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 18540377HCID 18540377, compound

Product 1

HCID 9936069HCID 9936069, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl isocyanate (18.8 mg, 0.25 mmol) in MeCN (2 mL) was added, together with K2CO3 (34.5 mg, 0.25 mmol), to a solution of 4-[1-(3,4-dimethoxyphenoxy)-4-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)-butyl]benzonitrile (Preparation H; 109.4 mg, 0.25 mmol) in chloroform (0.5 mL). The reaction mixture was stirred at rt for 4 days before being added to a solid phase extraction plug (SiO2, 0.5 g). The plug was washed with CHCl3:MeCN (2.5 mL of 80:20), and the product was finally eluted with CHCl3:MeOH (3×2.5 mL of 95:5) to give the title compound.

Workup

  1. additionbefore being added to a solid phase extraction plug (SiO2, 0.5 g)
  2. washThe plug was washed with CHCl3
  3. washMeCN (2.5 mL of 80:20), and the product was finally eluted with CHCl3

Sources & evidence

ORD record
ord-f3dffbab95334617aa8c16b66eb19ae0
Source dataset
uspto-grants-2007_01
Patent number
US07164017B2

Reaction notes

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