Sodium Iodide → HCID 178513594, compound

HRID 2206228Notes

Reaction equation

HRID 2206228 reaction equation
[C:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]2[C:13]3[C:14]([O:18]C)=[N:15][CH:16]=[CH:17][C:12]=3[N:11]([C@@H:20]3[CH2:25][CH2:24][C@H:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22][CH2:21]3)[N:10]=2)[CH:5]=1)(=[O:3])[NH2:2].[I-].[Na+].Cl[Si](C)(C)C.FC(F)(F)C(O)=O>C1COCC1.C(#N)C>[NH2:26][C@@H:23]1[CH2:24][CH2:25][C@H:20]([N:11]2[C:12]3[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C:13]=3[C:9]([C:6]3[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[S:8][CH:7]=3)=[N:10]2)[CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 6422Trifluoroacetic acidHCID 178494048HCID 178494048, compound

Product 1

HCID 178513594HCID 178513594, compoundYield 619.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl (cis-4-(3-(5-carbamoyl-3-thienyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-1-yl)cyclohexyl)carbamate (33.0 mg) in a mixed solvent of acetonitrile (2 ml) and THF (1 ml) were added sodium iodide (26.2 mg) and chloro(trimethyl)silane (0.089 ml), and the mixture was stirred at 50° C. for 1 hr. Trifluoroacetic acid (2 mL) was added thereto, and the mixture was stirred at 50° C. for additional 2 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol) to give the title compound (155 mg).

Workup

  1. stirringthe mixture was stirred at 50° C. for additional 2 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-c5fd490d588b444fa78a2ce0009213fe
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

Loading…