Ammonia → HCID 118207805, compound

HRID 2205635Notes

Reaction equation

HRID 2205635 reaction equation
[C:1]([C:3]1[C:4]([NH:15][C@H:16]([C:18]2[N:23]=[C:22]3[CH:24]=[CH:25][N:26]([CH3:27])[C:21]3=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]2)[CH3:17])=[N:5][C:6](S(C)(=O)=O)=[N:7][C:8]=1[CH2:9][CH3:10])#[N:2].[NH3:41]>O1CCOCC1.CCOC(C)=O>[NH2:41][C:6]1[N:5]=[C:4]([NH:15][C@H:16]([C:18]2[N:23]=[C:22]3[CH:24]=[CH:25][N:26]([CH3:27])[C:21]3=[CH:20][C:19]=2[N:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:30][CH2:29]2)[CH3:17])[C:3]([C:1]#[N:2])=[C:8]([CH2:9][CH3:10])[N:7]=1

Participants

5

Reactant 2

HCID 222Ammonia2×HCID 118214766HCID 118214766, compound

Product 1

HCID 118207805HCID 118207805, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
75 °C

Procedure

To a 10 mL vial were added tert-butyl (S)-4-(5-(1-((5-cyano-6-ethyl-2-(methylsulfonyl)pyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)piperazine-1-carboxylate (32 mg, 0.056 mmol) in dioxane (2 mL) along with 0.5 M ammonia in dioxane (6.09 μL, 0.281 mmol) to give a yellow solution. The vial was sealed and the reaction mixture was stirred overnight at 75° C. The next day LCMS indicated the reaction was incomplete. Additional NH3 solution (2 eq) was added and the reaction mixture was allowed to stir for 6 hours at 75° C. LCMS showed the reaction was mostly complete. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The product was purified by column chromatography (ISCO 4 g, 50-100% EtOAc/hexane gradient) to give the title compound as a yellow oil.

Workup

  1. customto give a yellow solution
  2. customThe vial was sealed
  3. stirringto stir for 6 hours at 75° C
  4. washwashed with saturated aqueous NH4Cl (3×)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by column chromatography (ISCO 4 g, 50-100% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-ae875f595faf4477bb0768c1b734aca7
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

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