Triacetoxyperiodinane → HCID 136252352, compound

HRID 710676Notes

Reaction equation

HRID 710676 reaction equation
[Cl:1][C:2]1[C:3]([C:27]2[NH:28][CH2:29][CH2:30][N:31]=2)=[N:4][N:5]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][C:13]3[N:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[N:18]=[CH:19][C:12]2=3)=[O:10])[C:6]=1[CH3:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CS(C)=O.C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:27]2[NH:31][CH:30]=[CH:29][N:28]=2)=[N:4][N:5]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][C:13]3[N:17]([C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)[N:18]=[CH:19][C:12]2=3)=[O:10])[C:6]=1[CH3:7]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 73336208HCID 73336208, compound

Product 1

HCID 136252352HCID 136252352, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[4-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-5-methyl-pyrazol-1-yl]-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone (45 mg, 0.1 mmol), Dess-Martin periodinane (80 mg, 0.2 mmol) in DMSO (1 mL) was heated at 80° C. for 1 hour. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 (20 mL) and washed with water (3×5 mL). The organic layer was dried (Na2SO4), filtered, concentrated in vacuo and purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give 2-[4-chloro-3-(1H-imidazol-2-yl)-5-methyl-pyrazol-1-yl]-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone as white powder (32 mg, 73%). 1H NMR (400 MHz, DMSO-d6) δ 8.09 (s, 1H), 7.60 (s, 2H), 7.52 (m, 2H), 7.30 (dd, J=8.8, 8.3 Hz, 2H), 5.49 (s, 2H), 3.90 (m, 2H), 2.82 (t, J=5.1 Hz, 2H), 2.22 (s, 3H), 1.95 (m, 2H); MS: (ES) m/z calculated for C21H20ClFN7O [M+H]+ 440.1, found 440.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (3×5 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record
ord-7613ff8597a24f3781b6998924d67b8e
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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