n-Heptyl isocyanate → Ethyl 3-{4-[4-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoate

HRID 1092283Notes

Reaction equation

HRID 1092283 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=2)[CH:4]=1.[CH2:22]([N:29]=[C:30]=[O:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[CH2:22]([NH:29][C:30](=[O:31])[N:2]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:14]=2)[CH:4]=1)[CH3:1])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 138341n-Heptyl isocyanateHCID 66591311Ethyl 3-[4-(4-methylaminopyrid-2-yl)phenyl]propanoate

Product 1

HCID 66591734Ethyl 3-{4-[4-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoateYield 97%

Procedure

270 mg (0.63 mmol, 1 eq) of ethyl 3-[4-(4-methylaminopyrid-2-yl)phenyl]propanoate are mixed with 0.6 mL (3.7 mmol, 6 eq) of heptyl isocyanate and then irradiated in a microwave machine for 2 times 30 minutes, while keeping the temperature constant at 100° C. The reaction mixture is chromatographed on silica gel (90/10 heptane/ethyl acetate). 260 mg of ethyl 3-{4-[4-(3-heptyl-1-methylureido)pyrid-2-yl]phenyl}propanoate are obtained. Yield=64%.

Workup

  1. customirradiated in a microwave machine for 2 times 30 minutes
  2. customconstant at 100° C
  3. customThe reaction mixture is chromatographed on silica gel (90/10 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5efceb909d67410d86deb50d241fd438
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

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