Fusaric Acid → (5-Butyl-pyridin-2-yl)-{4-[1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanone

HRID 1958380Notes

Reaction equation

HRID 1958380 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].ClC(OC(C)C)=O.Cl.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:36]3=[N:37][CH:38]=[N:39][C:40]([O:41][CH:42]4[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]4)=[C:35]3[CH:34]=[N:33]2)=[CH:28][CH:27]=1)(=[O:25])=[O:24].C(N(CC)CC)C>CN(C=O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([N:45]2[CH2:46][CH2:47][CH:42]([O:41][C:40]3[N:39]=[CH:38][N:37]=[C:36]4[N:32]([C:29]5[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:24])=[O:25])=[CH:31][CH:30]=5)[N:33]=[CH:34][C:35]=34)[CH2:43][CH2:44]2)=[O:13])=[N:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 3442Fusaric AcidHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 218977741-(4-Methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride

Product 1

HCID 21897785(5-Butyl-pyridin-2-yl)-{4-[1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-methanoneYield 14.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Butyl-pyridine-2-carboxylic acid (92 mg, 0.51 mmol) and isopropyl chloroformate (70 μL, 0.51 mmol) were dissolved in DMF and stirred at room temperature for 40 min. 1-(4-Methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (70 mg, 0.17 mmol) and triethylamine (72 μL, 0.51 mmol) were added next and continued to stir for 24 hours. Progress of the reaction was monitored by TLC and LCMS. Removal of organic solvents in vacuo and purification by HPLC afforded Compound A125 as a white solid (13 mg, 13%). Exact mass calculated for C22H30N6O4S 534.63, found 535.20 (MH+).

Workup

  1. stirringto stir for 24 hours
  2. customRemoval of organic solvents
  3. customin vacuo and purification by HPLC

Sources & evidence

ORD record
ord-49a3fc5e5da04a82b14236ff5ee9f892
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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