Potassium Carbonate → {1-[N'-(3-(2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-3-hydroxy-4-phenyl-butyl]-N'-(4-pyridin-3-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}carbamic acid methyl ester

HRID 1158536Notes

Reaction equation

HRID 1158536 reaction equation
[CH3:1][O:2][C:3](=[O:45])[NH:4][CH:5]([C:10]([NH:12][N:13]([CH2:37][C:38]1[CH:43]=[CH:42][C:41](Br)=[CH:40][CH:39]=1)[CH2:14][CH2:15][C:16]([C:25](=[O:36])[NH:26][CH:27]([C:32](=[O:35])[NH:33][CH3:34])[C:28]([CH3:31])([CH3:30])[CH3:29])([OH:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7].[N:46]1[CH:51]=[CH:50][CH:49]=[C:48](B(O)O)[CH:47]=1.[B-](F)(F)(F)F.CC([PH+](C(C)(C)C)C(C)(C)C)(C)C.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC.O>[CH3:1][O:2][C:3](=[O:45])[NH:4][CH:5]([C:10]([NH:12][N:13]([CH2:14][CH2:15][C:16]([C:25](=[O:36])[NH:26][CH:27]([C:32](=[O:35])[NH:33][CH3:34])[C:28]([CH3:31])([CH3:30])[CH3:29])([OH:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([C:48]2[CH:47]=[N:46][CH:51]=[CH:50][CH:49]=2)=[CH:40][CH:39]=1)=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 68677269(1-{N'-(4-Bromobenzyl)-N'-[3-(2,2-dimethyl-1-methylcarbamoyl-propylcarbamoyl)-3-hydroxy-4-phenyl-butyl]-hydrazinocarbonyl}2,2-dimethylpropyl)carbamic acid methyl ester

Product 1

HCID 68678997{1-[N'-(3-(2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-3-hydroxy-4-phenyl-butyl]-N'-(4-pyridin-3-yl-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}carbamic acid methyl esterYield 44%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of compound (53) (69 mg, 0.10 mmol), 3-pyridylboronic acid (37 mg, 0.30 mmol), Pd(OAc)2 (1.1 mg, 0.0050 mmol), [(t-Bu)3PH]BF4 (3.0 mg, 0.010 mmol) and K2CO3 (41.5 mg, 0.30 mmol), H2O (0.30 mL) and 1,2-dimethoxyethane (1.0 mL) in a 2.0 mL microwave vial was irradiated to 80° C. for 20 min. The reaction mixture was filtered through celite and the solvent evaporated under reduced pressure. The residue was purified by preparative RP-LC-MS which gave 30.1 mg of the title compound (44% yield) as a colorless solid.

Workup

  1. customwas irradiated to 80° C. for 20 min
  2. filtrationThe reaction mixture was filtered through celite
  3. customthe solvent evaporated under reduced pressure
  4. customThe residue was purified by preparative RP-LC-MS which

Sources & evidence

ORD record
ord-7985f5aee27a4790be518cda79701421
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

Loading…