Dimethylformamide → HCID 24905240, compound

HRID 238028Notes

Reaction equation

HRID 238028 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:20]([CH3:22])[CH3:21])[N:9]=[C:10]([C:11]3C=CC(F)=[C:15]([CH:18]=3)C#N)[C:3]=12.[CH3:23][C:24]([O-:27])(C)[CH3:25].[K+].[CH3:29][N:30](C=O)C>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:20]([CH3:22])[CH3:21])[N:9]=[C:10]([C:11]3[CH:18]=[CH:15][C:25]([C:29]#[N:30])=[C:24]([OH:27])[CH:23]=3)[C:3]=12

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 23665647Potassium tert-butoxideHCID 24905236HCID 24905236, compound

Product 1

HCID 24905240HCID 24905240, compound

Procedure

5-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluorobenzonitrile (BA151, 20 mg, 0.07 mmol) was dissolved in DMF (1 ml). t-BuOK (24 mg, 0.21 mmol) was added and the reaction was stirred at room temperature overnight. Reaction was then heated to 150° C. for 24 hours. The reaction was then concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA157—2 (7 mg), ESI-MS (M+H)+ m/z calcd 295.1, found 295.4 and BA157—3 (8 mg), ESI-MS (M+H)+ m/z calcd 310.1, found 310.4.

Workup

  1. customReaction
  2. temperaturewas then heated to 150° C. for 24 hours
  3. concentrationThe reaction was then concentrated in vacuo
  4. custompurified by RP-HPLC (MeCN:H2O:0.1% TFA)
  5. customto yield BA157—2 (7 mg), ESI-MS (M+H)+ m/z calcd 295.1

Sources & evidence

ORD record
ord-824c11d70c0a46859b2038fb99388f9c
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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