Diisopropylethylamine → 3-(1-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)ethyl)-4-phenyl-1H-isochromen-1-one

HRID 634458Notes

Reaction equation

HRID 634458 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH:18]([NH:20]C(=O)OC(C)(C)C)[CH3:19])[O:3]1.Cl[C:29]1[N:34]=[CH:33][N:32]=[C:31]2[NH:35][N:36]=[CH:37][C:30]=12.CCN(C(C)C)C(C)C>C(O)(C)(C)C>[NH:35]1[C:31]2=[N:32][CH:33]=[N:34][C:29]([NH:20][CH:18]([C:4]3[O:3][C:2](=[O:1])[C:11]4[C:6]([C:5]=3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH3:19])=[C:30]2[CH:37]=[N:36]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidineHCID 118131293tert-butyl 1-(1-oxo-4-phenyl-1H-isochromen-3-yl)ethylcarbamate2×

Product 1

HCID 1181313693-(1-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)ethyl)-4-phenyl-1H-isochromen-1-oneYield 56%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

3-(1-aminoethyl)-4-phenyl-1H-isochromen-1-one hydrochloride (Intermediate E1, 141 mg, 0.136 mmol), 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (42.0 mg, 0.272 mmol) and DIEA (95 μL, 0.543 mmol) were stirred at 80° C. for 3 hrs in tert-butanol (800 μL). The reaction was quenched by the addition of 1 mL of 1M HClaqueous and the resulting crude was straightforward purified via reverse phase chromatography using a Biotage C18 30 g SNAP with a gradient of water and acetonitrile to give the title compound (29 mg, 56%).

Workup

  1. customThe reaction was quenched by the addition of 1 mL of 1M HClaqueous
  2. customthe resulting crude was straightforward purified via reverse phase chromatography

Sources & evidence

ORD record
ord-f5bc9197cc8b467790a1bf65edf1bda4
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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