Chloride → HCID 136237265, compound

HRID 1852031Notes

Reaction equation

HRID 1852031 reaction equation
[Cl-].[C:2](=[O:5])([O-])[OH:3].[Na+].[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2[C:30]3[C:25](=[CH:26][C:27]([C:31]([NH:33][C@H:34]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([CH:42]([CH3:44])[CH3:43])[CH:37]=4)[CH3:35])=[O:32])=[CH:28][CH:29]=3)[C:24]([CH3:45])=[C:23]2[CH3:46])=[CH:17][CH:16]=1)#[N:8].[N:47]12CCCN=C1CCCCC2>C(OCC)(=O)C.CS(C)=O>[CH:42]([C:38]1[CH:37]=[C:36]([C@@H:34]([NH:33][C:31]([C:27]2[CH:26]=[C:25]3[C:30](=[CH:29][CH:28]=2)[N:22]([CH2:21][C:18]2[CH:17]=[CH:16][C:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[C:7]4[NH:47][C:2](=[O:5])[O:3][N:8]=4)=[CH:20][CH:19]=2)[C:23]([CH3:46])=[C:24]3[CH3:45])=[O:32])[CH3:35])[CH:41]=[CH:40][CH:39]=1)([CH3:43])[CH3:44]

Participants

7

Reactant 4

HCID 312ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 71074766HCID 71074766, compound

Product 1

HCID 136237265HCID 136237265, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of hydroxylammoium chloride (0.2 g, 2.88 mmol), sodium hydrogen carbonate (0.3 g, 3.57 mmol) and dimethyl sulfoxide (2 mL) was stirred at 40° C. for 30 min. (S)-1-((2′-cyano-[1,1′-biphenyl]-4-yl)methyl)-N-(1-(3-isopropylphenyl)ethyl)-2,3-dimethyl-1H-indole-5-carboxamide (0.1 g, 0.19 mmol) was added, and the mixture was stirred at 90° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with brine, and dried over anhydrous sodium sulfate. Thvent was evaporated under reduced pressure, and the residue was dissolved in THF (3 mL), N,N′-carbonyldiimidazole (0.055 g, 0.29 mmol) and then 1,8-diazabicyclo[5,4,0]undec-7-ene (0.05 mL, 0.29 mmol) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous potassium hydrogensulfate solution and then with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by preparative-HPLC to obtain the title compound. ESI-MS (m/z): 585 [M+H]+.

Workup

  1. additionwas added
  2. washwashed with water
  3. dry with materialwith brine, and dried over anhydrous sodium sulfate
  4. customThvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in THF (3 mL)
  6. stirringthe mixture was stirred at room temperature for 2 hr
  7. washwashed with saturated aqueous potassium hydrogensulfate solution
  8. dry with materialwith brine, and dried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by preparative-HPLC

Sources & evidence

ORD record
ord-0ada0ef287bd45cb8e8ae97aebc92990
Source dataset
uspto-grants-2015_02
Patent number
US08957093B2

Reaction notes

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