Tetrahydrofuran → 1,1-Dimethylethyl 4-{5-chloro-6-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate

HRID 2064190Notes

Reaction equation

HRID 2064190 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.[O:27]1CCC[CH2:28]1>>[Cl:8][C:6]1[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]2[N:13]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]3)[C:28](=[O:27])[NH:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 598501671,1-Dimethylethyl 4-({2-amino-4-chloro-5-[(1-methylethyl)oxy]phenyl}amino)-1-piperidinecarboxylate

Product 1

HCID 598501801,1-Dimethylethyl 4-{5-chloro-6-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylateYield 65%

Conditions

Temperature
50 °C

Procedure

A solution of 1,1-dimethylethyl 4-({2-amino-4-chloro-5-[(1-methylethyl)oxy]phenyl}amino)-1-piperidinecarboxylate (D85, 200 mg, 0.52 mmol) in tetrahydrofuran (2 ml) was treated with N,N′-carbonyldiimidazole (125 mg, 0.78 mmol) and heated at 50° C. for 17 hrs. The mixture was concentrated under vacuum and the residue treated with Na2CO3 solution (5 ml) and extracted with ethyl acetate (2×10 ml). The combined extract was dried (MgSO4), concentrated under vacuum to leave the title compound as an oil (140 mg, 65%). M+−H=408.2.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue treated with Na2CO3 solution (5 ml)
  3. extractionextracted with ethyl acetate (2×10 ml)
  4. extractionThe combined extract
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-58d79b0f674c4762a8dd29ec4d678428
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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