Acetonitrile → HCID 69811962, compound

HRID 1916144Notes

Reaction equation

HRID 1916144 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].[C:39](#[N:41])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[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]([C:39]#[N:41])[N:13]=2)[CH2:6]1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 58177355HCID 58177355, compound

Product 1

HCID 69811962HCID 69811962, compound

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Procedure

A solution 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 derived from Example 84, step 1 was treated with tetra-n-butyl ammonium cyanide in acetonitrile at 100° C. for 4 hours. Solvent was concentrated to dryness and purified by chromatography to give a protected intermediate that was de-protected similar to step 5, Example 76, to give 4-((S)-1-methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2-carbonitrile. MS: ES+: 399

Workup

  1. concentrationSolvent was concentrated to dryness
  2. custompurified by chromatography
  3. customto give a protected intermediate

Sources & evidence

ORD record
ord-932a2b08d7f74bf5a3f8069b2c5d41de
Source dataset
uspto-grants-2013_12
Patent number
US08618103B2

Reaction notes

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