Isopropyl chloroformate → {4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-(5-morpholin-4-ylmethyl-furan-2-yl)-methanone

HRID 1864155

Reaction equation

HRID 1864155 reaction equation
[N:1]1([CH2:7][C:8]2[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(OC(Cl)=O)(C)C.C(N(CC)CC)C.[CH3:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([N:40]2[C:44]3=[N:45][CH:46]=[N:47][C:48]([O:49][CH:50]4[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]4)=[C:43]3[CH:42]=[N:41]2)=[CH:36][CH:35]=1)(=[O:33])=[O:32]>CS(C)=O>[CH3:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([N:40]2[C:44]3=[N:45][CH:46]=[N:47][C:48]([O:49][CH:50]4[CH2:55][CH2:54][N:53]([C:13]([C:11]5[O:12][C:8]([CH2:7][N:1]6[CH2:2][CH2:3][O:4][CH2:5][CH2:6]6)=[CH:9][CH:10]=5)=[O:15])[CH2:52][CH2:51]4)=[C:43]3[CH:42]=[N:41]2)=[CH:36][CH:35]=1)(=[O:32])=[O:33]

Participants

6

Reactant 4

HCID 7917Isopropyl chloroformateHCID 8471Triethylamine2×HCID 5805305-Morpholin-4-ylmethyl-furan-2-carboxylic acidHCID 113608021-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 21897743{4-[1-(4-Methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidin-1-yl}-(5-morpholin-4-ylmethyl-furan-2-yl)-methanone

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Morpholin-4-ylmethyl-furan-2-carboxylic acid (0.12 mmol, 25 mg), and isopropylchloroformate (0.12 mmol, 17 μL) and triethylamine (0.12 mmol, 17 μL) were dissolved in DMSO (2 mL) and stirred for 30 minutes at room temperature. Then, 1-(4-methanesulfonyl-phenyl)-4-(piperidin-4-yloxy)-1H-pyrazolo[3,4-d]pyrimidine (0.12 mmol, 50 mg) and excess triethylamine were added. The mixture was heated in a microwave for 5 minutes at 120° C. The progress of the reaction was monitored by thin layer chromatography and LCMS. Purification by HPLC provided compound A116 as a white solid. LCMS (ESI), m/z 567.3 (MH+, 100%).

Workup

  1. temperatureThe mixture was heated in a microwave for 5 minutes at 120° C
  2. customPurification by HPLC
  3. customprovided compound

Sources & evidence

ORD record
ord-7ae68b471c4247deacda4aac7a03b9ab
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Linked notes

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