Bis-(1H-imidazol-2-YL)-methanone → HCID 59850132, compound

HRID 2064150Notes

Reaction equation

HRID 2064150 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1.[C:24](C1NC=CN=1)(C1NC=CN=1)=[O:25]>O1CCCC1>[F:8][C:6]1[C:5]([Br:9])=[CH:4][C:3]2[N:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:24](=[O:25])[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 59850151HCID 59850151, compound

Product 1

HCID 59850132HCID 59850132, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-Dimethylethyl 4-[(2-amino-4-fluoro-5-bromophenyl)amino]-1-piperidinecarboxylate (D44) (0.83 g, 2.1 mmole) was dissolved in anhydrous tetrahydrofuran (20 ml) and carbonyl diimidazole (0.51 g, 3.2 mmole) was added in portions over 15 minutes. The mixture was stirred at rt for 1 hr and the at reflux temperature for 18 hrs. The cooled mixture was concentrated to dryness under vacuum and the residue purified by silica gel chromatography eluting with 15-100% ethyl acetate in n-pentane to afford the title compound as a buff solid, 0.54 g, 51% LC/MS—85% m/e 412/414 (MH−).

Workup

  1. temperaturethe at reflux temperature for 18 hrs
  2. concentrationThe cooled mixture was concentrated to dryness under vacuum
  3. customthe residue purified by silica gel chromatography
  4. washeluting with 15-100% ethyl acetate in n-pentane

Sources & evidence

ORD record
ord-64b81d11dfcb42e3b24a8e8e18b090a8
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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