1,4-Dioxane--water (1/1) → HCID 178504938, compound

HRID 1916133Notes

Reaction equation

HRID 1916133 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].O.[O:40]1CCOCC1>>[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]([OH:40])[N:13]=2)[CH2:6]1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 218864351,4-Dioxane--water (1/1)HCID 58177355HCID 58177355, compound

Product 1

HCID 178504938HCID 178504938, compound

Procedure

A solution of ((S)-1-methanesulfonyl-piperidin-3-yl)-[2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine (18 mg, 0.044 mmol) from Example 84, step 1, in water/dioxane was heated to 105° C. for 16 hr. Solvent was evaporated and the product purified by super critical chromatography (SFC) to give 4-((S)-1-methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-ol. MS (ES+): 390.

Workup

  1. customSolvent was evaporated
  2. customthe product purified by super critical chromatography (SFC)

Sources & evidence

ORD record
ord-8c1b4b0389e44317a2bf55033375d96a
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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