Methyl chloroformate → HCID 118390794, compound

HRID 590870Notes

Reaction equation

HRID 590870 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([NH2:30])=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.Cl[C:32]([O:34][CH3:35])=[O:33]>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([NH:30][C:32](=[O:33])[O:34][CH3:35])=[N:9][N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 118272274HCID 118272274, compound

Product 1

HCID 118390794HCID 118390794, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL round bottom flask charged with 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (1500 mg, 3.65 mmol) in DCM (30 ml) and pyridine (3 mL) was cooled to 0° C. using an ice bath. Methyl chloroformate (0.564 ml, 7.30 mmol) was added and the reaction mixture was stirred for 16 h warming to ambient temperature. The mixture was washed with saturated copper sulfate solution (2×50 mL), dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel (ISCO; 40 g prepacked) eluting with ethyl acetate/hexanes to afford methyl (6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate (1492 mg, 3.18 mmol, 87% yield) as a white solid. MS ESI calc'd. For C27H22ClN4O2 [M+H]+ 469. found 469.

Workup

  1. temperaturewarming to ambient temperature
  2. washThe mixture was washed with saturated copper sulfate solution (2×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe resulting residue was purified by flash column chromatography on silica gel (ISCO; 40 g prepacked)
  7. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2ef3986980cc4f2894582dcda727c845
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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