Sodium Cyanide → [(S)-2-(7-Cyanomethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

HRID 1453898Notes

Reaction equation

HRID 1453898 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25]O)=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[C-:33]#[N:34].[Na+].C(=O)(O)[O-].[Na+]>ClCCl.CS(C)=O>[CH2:1]([O:8][C:9](=[O:28])[NH:10][C@@H:11]([CH3:27])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]3[O:24][C:23]([CH2:25][C:33]#[N:34])=[CH:22][C:20]3=2)[CH:15]=[N:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8929Sodium CyanideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68855697[(S)-2-(7-Hydroxymethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

Product 1

HCID 68857442[(S)-2-(7-Cyanomethyl-furo[2,3-g]indazol-1-yl)-1-methylethyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Example 2, Step B (0.55 g, 1.45 mmol) in dichloromethane (20 mL) was cooled (ice bath), thionyl chloride (0.16 mL, 2.18 mmol) was added, and the mixture was stirred for thirty minutes. The reaction mixture was evaporated to a residue which was dissolved in dichloromethane (20 mL) and evaporated. A solution of sodium cyanide (0.29 g, 5.8 mmol) in DMSO (10 mL) was added to this residue and the mixture was stirred at room temperature for one hour. Saturated aqueous sodium bicarbonate (100 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with saturated aqueous sodium bicarbonate (2×150 mL), dried (MgSO4) and evaporated to a tan solid (0.49 g, 87%): LC/MS m/z 389 [M+H]+.

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated to a residue which
  3. dissolutionwas dissolved in dichloromethane (20 mL)
  4. customevaporated
  5. stirringthe mixture was stirred at room temperature for one hour
  6. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  7. washThe combined extracts were washed with saturated aqueous sodium bicarbonate (2×150 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated to a tan solid (0.49 g, 87%)

Sources & evidence

ORD record
ord-11a8ce3e831b4286b8bab1c8355a9679
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Reaction notes

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