Cyclohexylamine → HCID 24831033, compound

HRID 2410052Notes

Reaction equation

HRID 2410052 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[CH2:11][C:10](=[O:14])[N:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])[C:8]2=[O:25])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:26]([CH:29](CCCC)[C:30]([O:32]CC)=[O:31])=[C:27]=[O:28].C1(N)CCCCC1.C(Cl)(=O)CC(Cl)=O>ClCCl>[C:30]([CH2:29][NH:26][C:27]([C:11]1[C:12](=[O:13])[N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:8](=[O:25])[N:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:10]=1[OH:14])=[O:28])([OH:32])=[O:31]

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 74269Propanedioyl dichlorideHCID 68636634HCID 68636634, compoundHCID 86762632HCID 86762632, compound

Product 1

HCID 24831033HCID 24831033, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 6-(3-cyclohexyl-2,4,6-trioxotetrahydro-1(2H)-pyrimidinyl)hexanoate. Ethyl isocyanatohexanoate (790 mg, 4.26 mmoles) and cyclohexylamine (490 uL, 4.26 mmoles) were stirred together in dichloromethane (100 mL) for 2 hours. Malonyl dichloride (414 uL, 4.26 mmoles) was added and the mixture was heated under gentle reflux for 2 hours. The mixture was purified by flash chromatography (dichloromethane to 5% methanol in dichloromethane) to give the title compound (1.07 g, 71%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.56-4.67 (m, 1 H), 4.62 (tt, J=12.25, 3.79 Hz, 1 H), 4.13 (q, J=7.24 Hz, 2 H), 3.85 (t, 2 H), 2.31 (t, 2 H), 2.26 (dq, 2 H), 1.85 (d, J=13.39 Hz, 2 H), 1.57-1.73 (m, 7 H), 1.29-1.43 (m, 4 H), 1.26 (t, J=7.07 Hz, 3 H), 1.06-1.24 (m, 2 H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder gentle reflux for 2 hours
  3. customThe mixture was purified by flash chromatography (dichloromethane to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a8f40f2a7a954362ae146af589c6e610
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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