Diisopropylethylamine → HCID 121393696, compound

HRID 1480032Notes

Reaction equation

HRID 1480032 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[C:5](=[O:17])[NH:4][C:3]=1[C:18]1[N:19]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[CH:20]=[CH:21][N:22]=1.CCN(C(C)C)C(C)C.[CH:40]1([N:45]=[C:46]=[O:47])[CH2:44][CH2:43][CH2:42][CH2:41]1>C(Cl)Cl>[CH:40]1([NH:45][C:46]([N:4]2[C:3]([C:18]3[N:19]([C:23]4[CH:24]=[CH:25][C:26]([C:27]#[N:28])=[CH:29][CH:30]=4)[CH:20]=[CH:21][N:22]=3)=[C:2]([CH3:1])[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=3)[C:5]2=[O:17])=[O:47])[CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 643500Cyclopentyl IsocyanateHCID 121393699HCID 121393699, compound

Product 1

HCID 121393696HCID 121393696, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

4-[5′-Methyl-2′-oxo-1′-(3-trifluoromethyl-phenyl)-2′,3′-dihydro-1′H-[2,4′]biimidazolyl-1-yl]-benzonitrile (Example 59, 108 mg, 0.26 mmol) was suspended in dry DCM (5 ml) and DIPEA (130 μl, 3 eq.) was added followed by cyclopentyl isocyanate (90 μl, 88 mg, 0.79 mmol). The mixture was heated and stirred at 45° C. for 24 h. The solvent was removed in vacuo and the residue purified by chromatography eluting with EtOAc, thereby yielding the title compound (100 mg, 73%).

Workup

  1. temperatureThe mixture was heated
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by chromatography
  4. washeluting with EtOAc

Sources & evidence

ORD record
ord-f3a7544ba0af4c12824700a7d18ff654
Source dataset
uspto-grants-2016_08
Patent number
US09409870B2

Reaction notes

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