Propanal → HCID 66754902, compound

HRID 1643971Notes

Reaction equation

HRID 1643971 reaction equation
[Cl:1][C:2]1[CH:43]=[CH:42][C:5]2[N:6]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[C:7](=[O:30])[N:8]([CH:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:10](=[O:23])[N:11]3[CH2:16][CH2:15][N:14]([CH:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.[CH:44](=O)[CH2:45][CH3:46]>C1COCC1>[Cl:1][C:2]1[CH:43]=[CH:42][C:5]2[N:6]([S:31]([C:34]3[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=3)(=[O:33])=[O:32])[C:7](=[O:30])[N:8]([CH:9]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:10](=[O:23])[N:11]3[CH2:12][CH2:13][N:14]([CH:17]4[CH2:18][CH2:19][N:20]([CH2:44][CH2:45][CH3:46])[CH2:21][CH2:22]4)[CH2:15][CH2:16]3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 527PropanalHCID 66754782HCID 66754782, compound

Product 1

HCID 66754902HCID 66754902, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 52 mg (0.08 mmol) of 5-chloro-1-(4-methoxybenzenesulfonyl)-3-[2-oxo-1-phenyl-2-(4-piperidin-4-ylpiperazin-1-yl)-ethyl]-1,3-dihydrobenzimidazol-2-one (Example 128) in 3 ml of THF was mixed with 5.32 mg (0.09 mmol) of propionaldehyde and 70 mg of MP-triacetoxyborohydrde resin (Argonaut, 2.55 mmol/g, 0.17 mmol) and shaken at room temperature overnight. The solid phase reagent was filtered off and washed with dichloromethane. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase gradient 8-11% methanol in dichloromethane). Yield: 33.2 mg (60%) of colorless solid

Workup

  1. filtrationThe solid phase reagent was filtered off
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (mobile phase gradient 8-11% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a6125018492c4a92afb2502d6c6717b3
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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