Acetonitrile → HCID 118214766, compound

HRID 2205634Notes

Reaction equation

HRID 2205634 reaction equation
[C:1]([C:3]1[C:4]([NH:13][C@H:14]([C:16]2[N:21]=[C:20]3[CH:22]=[CH:23][N:24]([CH3:25])[C:19]3=[CH:18][C:17]=2[N:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)[CH3:15])=[N:5][C:6](SC)=[N:7][C:8]=1[CH2:9][CH3:10])#[N:2].O[O:40][S:41]([O-:43])=O.[K+].[C:45](#N)C>O.CCOC(C)=O>[C:1]([C:3]1[C:4]([NH:13][C@H:14]([C:16]2[N:21]=[C:20]3[CH:22]=[CH:23][N:24]([CH3:25])[C:19]3=[CH:18][C:17]=2[N:26]2[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:33])[CH2:30][CH2:31]2)[CH3:15])=[N:5][C:6]([S:41]([CH3:45])(=[O:43])=[O:40])=[N:7][C:8]=1[CH2:9][CH3:10])#[N:2]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 23707502Potassium hydroxy sulfiteHCID 118207803HCID 118207803, compound

Product 1

HCID 118214766HCID 118214766, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a 20 mL round-bottom flask were added (S)-tert-butyl 4-(5-(1-((5-cyano-6-ethyl-2-(methylthio)pyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)piperazine-1-carboxylate (78 mg, 0.145 mmol) in acetonitrile (1.5 mL) and water (1.5 mL) along with OXONE® (223 mg, 0.363 mmol) at 0° C. The reaction mixture was allowed to stir for 30 minutes at 0° C. and then for 3.5 hours at room temperature. LCMS indicated the reaction was mostly complete. The reaction mixture was diluted with EtOAc and washed with brine (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The product was purified by column chromatography (ISCO 4 g, 30-100% EtOAc/hexane gradient) to give the title compound as a yellow oil. ESI-MS m/z [M+H]+ calc'd for C27H36N8O4S, 569. found 569.

Workup

  1. waitfor 3.5 hours at room temperature
  2. washwashed with brine (3×)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography (ISCO 4 g, 30-100% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-23fa0249992146ff93bf89d0c62274e4
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

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