Acetaldehyde → HCID 66755649, compound

HRID 1631994Notes

Reaction equation

HRID 1631994 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]2[N:6]([S:30]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:7](=[O:29])[N:8]([CH:9]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10](=[O:22])[N:11]3[CH2:15][CH2:14][C@H:13]([N:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[CH2:12]3)[C:4]=2[CH:3]=1.[CH:43](=O)[CH3:44].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>C1COCC1>[Cl:1][C:2]1[CH:42]=[CH:41][C:5]2[N:6]([S:30]([C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)(=[O:32])=[O:31])[C:7](=[O:29])[N:8]([CH:9]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:10]([N:11]3[CH2:15][CH2:14][C@H:13]([N:16]4[CH2:17][CH2:18][N:19]([CH2:43][CH3:44])[CH2:20][CH2:21]4)[CH2:12]3)=[O:22])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 2724942TriacetoxyborohydrideHCID 66754901HCID 66754901, compound

Product 1

HCID 66755649HCID 66755649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 99.0 mg (0.16 mmol) of 5-chloro-1-(4-methoxybenzenesulfonyl)-3-[2-oxo-1-phenyl-2-((S)-3-piperazin-1-yl-pyrrolidin-1-yl)ethyl]-1,3-dihydrobenzimidazol-2-one (example 149) in 4 ml of THF was mixed with 7.15 mg (0.16 mmol) of acetaldehyde and 160 mg of MP-triacetoxyborohydride resin (Argonaut, 2.55 mmol/g, 0.41 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 preparative RP-HPLC (mobile phase: gradient from 10% to 80% acetonitrile in water, 0.1% trifluoroacetic acid as modulator). Yield: 38.6 mg (38%) 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 preparative RP-HPLC (mobile phase: gradient from 10% to 80% acetonitrile in water, 0.1% trifluoroacetic acid as modulator)

Sources & evidence

ORD record
ord-cb783ef49a744d1d897d04683a293e76
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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