Ammonium Hydroxide → HCID 58177247, compound

HRID 1916125Notes

Reaction equation

HRID 1916125 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([NH:11][C:12]2[C:17]([C:18]3[N:19]=[C:20]4[CH:26]=[CH:25][N:24](COCC[Si](C)(C)C)[C:21]4=[N:22][CH:23]=3)=[CH:16][N:15]=[C:14](S(C)(=O)=O)[N:13]=2)[CH2:6]1)(=[O:4])=[O:3].[OH-].[NH4+:40]>O1CCOCC1>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][C@H:7]([NH:11][C:12]2[C:17]([C:18]3[N:19]=[C:20]4[CH:26]=[CH:25][NH:24][C:21]4=[N:22][CH:23]=3)=[CH:16][N:15]=[C:14]([NH2:40])[N:13]=2)[CH2:6]1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 58177355HCID 58177355, compound

Product 1

HCID 58177247HCID 58177247, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of ((S)-1-methanesulfonyl-piperidin-3-yl)-{2-methanesulfonyl-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-amine from Example 84, step 1 in ammonium hydroxide in dioxane was heated at 90° C. for 6 hours. The reaction was concentrated and diluted with water and extracted with EtOAc (2×20 ml). The organic layers were dried over MgSO4 and concentrated in vacuo to give a yellow foaming solid. MS (ES+): 561. The de-protection step was similar to step 5 of Example 76 to give N*4*-((S)-1-methanesulfonyl-piperidin-3-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine. MS (ES+): 389.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc (2×20 ml)
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a yellow foaming solid

Sources & evidence

ORD record
ord-cb6cfb07e0ae4037944de5b5116f90e1
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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