Triethylamine → n-(3-Acetylphenyl)-n'-((3s,4s)-4-{[4-(4-fluorobenzyl)cyclohexyl]amino}tetrahydro-3-furanyl)urea

HRID 397167Notes

Reaction equation

HRID 397167 reaction equation
Cl.Cl.[F:3][C:4]1[CH:23]=[CH:22][C:7]([CH2:8][CH:9]2[CH2:14][CH2:13][CH:12]([NH:15][C@H:16]3[C@H:20]([NH2:21])[CH2:19][O:18][CH2:17]3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:31]([C:34]1[CH:35]=[C:36]([N:40]=[C:41]=[O:42])[CH:37]=[CH:38][CH:39]=1)(=[O:33])[CH3:32]>ClCCl>[C:31]([C:34]1[CH:35]=[C:36]([NH:40][C:41]([NH:21][C@H:20]2[C@H:16]([NH:15][CH:12]3[CH2:11][CH2:10][CH:9]([CH2:8][C:7]4[CH:6]=[CH:5][C:4]([F:3])=[CH:23][CH:22]=4)[CH2:14][CH2:13]3)[CH2:17][O:18][CH2:19]2)=[O:42])[CH:37]=[CH:38][CH:39]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3127181-(3-Isocyanatophenyl)ethan-1-oneHCID 69587943(3S,4S)-N3-[4-(4-fluorobenzyl)cyclohexyl]tetrahydro-3,4-furandiamine dihydrochloride

Product 1

HCID 9911755n-(3-Acetylphenyl)-n'-((3s,4s)-4-{[4-(4-fluorobenzyl)cyclohexyl]amino}tetrahydro-3-furanyl)ureaYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (3S,4S)-N3-[4-(4-fluorobenzyl)cyclohexyl]tetrahydro-3,4-furandiamine dihydrochloride (20 mg, 0.055 mmol) and triethylamine (100 μL, 0.72 mmol) in dichloromethane (1 mL) was added 3-acetylphenyl isocyanate (7.1 mg, 0.050 mmol). The resulting solution was immediately concentrated, and the resulting residue was purified by flash column chromatography (100% ethyl acetate then 5% triethylamine in ethyl acetate then 10% methanol in ethylacetate containing 5% triethylamine) to yield the desired urea (15 mg, 60%) as an oily white solid. MS (ESI) 454 (M+H).

Workup

  1. concentrationThe resulting solution was immediately concentrated
  2. customthe resulting residue was purified by flash column chromatography (100% ethyl acetate

Sources & evidence

ORD record
ord-79ed37a1ec004b98a90c5fb1c55d44a1
Source dataset
uspto-grants-2003_08
Patent number
US06608227B1

Reaction notes

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