Imidazole → benzyl(4-(((tert-butyldimethylsilyl)oxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate

HRID 588205Notes

Reaction equation

HRID 588205 reaction equation
[CH2:1]([O:8][C:9](=[O:43])[NH:10][C:11]1[N:16]=[C:15]([CH2:17][OH:18])[C:14]2[C:19]([O:41][CH3:42])=[N:20][N:21]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:13]=2[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.CN(C=O)C.[C:54]([Si:58]([CH3:61])([CH3:60])Cl)([CH3:57])([CH3:56])[CH3:55]>C(OCC)(=O)C>[CH2:1]([O:8][C:9](=[O:43])[NH:10][C:11]1[N:16]=[C:15]([CH2:17][O:18][Si:58]([C:54]([CH3:57])([CH3:56])[CH3:55])([CH3:61])[CH3:60])[C:14]2[C:19]([O:41][CH3:42])=[N:20][N:21]([C:22]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:13]=2[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chloride2×HCID 118371771benzyl(4-(hydroxymethyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate

Product 1

HCID 123992626benzyl(4-(((tert-butyldimethylsilyl)oxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamateYield 92.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 50 mL round bottom flask charged with benzyl(4-(hydroxymethyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (180 mg, 0.315 mmol), imidazole (42.9 mg, 0.631 mmol) and DMF (3 ml) was added tert-butyldimethylchlorosilane (57.1 mg, 0.379 mmol). The flask was capped and the contents stirred at room temperature for 2 h. LCMS analysis indicated 80% conversion to the desire product. Excess tert-butyldimethylchlorosilane (25 mg) was added, and the reaction mixture stirred at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate (20 mL), washed with water (2×30 mL), dried (MgSO4) and filtered. The solvent was evaporated under reduced pressure to afford crude benzyl(4-(((tert-butyldimethylsilyl)oxy)methyl)-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (199 mg, 0.291 mmol, 92% yield) as a colorless oil. MS: [M+H]+ m/z 685.

Workup

  1. customThe flask was capped
  2. stirringthe reaction mixture stirred at room temperature for 16 h
  3. washwashed with water (2×30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-064410b96aae484999e3b8d9b2a5bf70
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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