Imidazole → HCID 131734500, compound

HRID 590879Notes

Reaction equation

HRID 590879 reaction equation
C1N=CN([C:6]([N:8]2[CH:12]=[N:11]C=C2)=[O:7])C=1.[Cl:13][C:14]1[N:19]=[CH:18][C:17]2C(N)=N[N:22]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:16]=2[CH:15]=1.N1C=CN=C1.[F:48][CH:49]([F:52])[CH2:50][OH:51]>O1CCCC1>[F:48][CH:49]([F:52])[CH2:50][O:51][C:6](=[O:7])[NH:8][C:12]1[C:17]2[CH:18]=[N:19][C:14]([Cl:13])=[CH:15][C:16]=2[N:22]([C:23]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:11]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 1361872,2-Difluoroethan-1-olHCID 118272274HCID 118272274, compound

Product 1

HCID 131734500HCID 131734500, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

CDI (395 mg, 2.434 mmol) was added to a stirred, room temperature mixture of 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (500 mg, 1.217 mmol) 6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine and imidazole (331 mg, 4.87 mmol) in tetrahydrofuran (12 mL), and the mixture was stirred at room temperature for overnight. 2,2-Difluoroethanol (0.231 mL, 3.65 mmol) was added to the mixture, and the resultant mixture was kept stirring at room temperature for 2 h before the reaction mixture was heated up to 60° C. for overnight. The mixture was cooled and concentrated, and the residue was loaded directly purified with silica gel column chromatography eluting with EtOAc/isohexane=25%, to give 2,2-difluoroethyl(6-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate (570 mg, 1.098 mmol, 90% yield) as a white solid. MS ESI calc'd. for C28H22ClF2N4O2 [M+H]+ 519. found 519.

Workup

  1. temperaturewas heated up to 60° C. for overnight
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. customthe residue was loaded directly purified with silica gel column chromatography
  5. washeluting with EtOAc/isohexane=25%

Sources & evidence

ORD record
ord-4b804afec0b1488093d3fe0e264a798f
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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