Potassium Carbonate → tert-butyl 3-((4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

HRID 1750940Notes

Reaction equation

HRID 1750940 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].I[CH2:39][CH2:40][CH2:41][N:42]1[C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=2[NH:44][C:43]1=[O:51]>CN(C)C=O.C(OCC)(=O)C>[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:39][CH2:40][CH2:41][N:42]3[C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=4[NH:44][C:43]3=[O:51])[CH2:8][CH2:7]2)[N:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13564030HCID 13564030, compoundHCID 58046667Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 58046630tert-butyl 3-((4-oxo-8-(3-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 59.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (1.2 g, 2.84 mmol) and potassium carbonate (0.59 g, 4.3 mmol) in N,N-dimethylformamide (20 mL), was added 1-(3-iodopropyl)-1,3-dihydro-2H-benzimidazol-2-one (0.86 g, 2.84 mmol). After stirring at 55° C. for 5 hours, the reaction mixture was diluted with ethyl acetate (100 mL), washed with water and brine. The organic phase was dried over MgSO4, filtered, concentrated and isolated by Biotage flash chromatography (2-10% methanol/dichloromethane) to obtain the title compound (1 g, 59%); 1H NMR (DMSO-d6): δ 1.51 (s, 9H), 1.60 (d, 2H, J=13.2 Hz), 1.82 (t, 2H, J=6.4 Hz), 2.35 (t, 2H, J=6.4 Hz), 2.53-2.60 (m, 4H), 2.65-2.71 (m, 4H), 3.85 (t, 2H, J=6.8 Hz), 4.56-4.60 (m, 2H), 6.76 (t, 1H, J=14.4 Hz), 6.85 (d, 2H, J=8 Hz), 6.95-6.97 (m, 3H), 7.17-7.24 (m, 3H), 7.48-7.54 (m, 2H), 7.78 (s, 1H), 7.82 (dt, 1H, J=7.2 and 1.6 Hz) 10.81 (s, 1H); MS for C35H41N5O4 m/z 596 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customisolated by Biotage flash chromatography (2-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-ce90a903e3b1449980c6a274be295b5d
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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