Ethylamine → HCID 121393712, compound

HRID 1480025Notes

Reaction equation

HRID 1480025 reaction equation
ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[CH3:14][C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[C:18](=[O:30])[NH:17][C:16]=1[C:31]1[N:35]([C:36]2[CH:43]=[CH:42][C:39]([C:40]#[N:41])=[CH:38][CH:37]=2)[N:34]=[CH:33][CH:32]=1.[CH2:44]([N:46]([CH2:49]C)CC)[CH3:45].C(N)C>C(Cl)Cl.C1COCC1>[C:40]([C:39]1[CH:38]=[CH:37][C:36]([N:35]2[C:31]([C:16]3[N:17]([C:49]([NH:46][CH2:44][CH3:45])=[O:3])[C:18](=[O:30])[N:19]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)[C:15]=3[CH3:14])=[CH:32][CH:33]=[N:34]2)=[CH:43][CH:42]=1)#[N:41]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 121393736HCID 121393736, compound

Product 1

HCID 121393712HCID 121393712, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrophenyl chloroformate (226 mg, 1.12 mmol) was added portion wise to a solution of 4-(5-{5-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrile (Example 1) (409 mg, 1.0 mmol) and triethylamine (0.355 mL, 2.55 mmol) in DCM (12 mL) under a nitrogen atmosphere. The mixture was stirred for 2.75 h giving a yellow solution. A solution of ethylamine (3.0 mL of a 2M solution in THF, 6 mmol) was added. The mixture was stirred for a further 2.5 h then concentrated in vacuo. The residue was chromatographed on silica gel eluting with 10-40% EtOAc in DCM then recolumned on silica gel with 25-60% EtOAc in cyclohexane to afford the title compound as a colourless foam after drying in vacuo.

Workup

  1. customgiving a yellow solution
  2. stirringThe mixture was stirred for a further 2.5 h
  3. concentrationthen concentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 10-40% EtOAc in DCM

Sources & evidence

ORD record
ord-799b348ccd104d9886ef3d14cf95a719
Source dataset
uspto-grants-2016_08
Patent number
US09409870B2

Reaction notes

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