Diisopropylethylamine → 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5-trimethyl-4-pyridin-3-ylmethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridine

HRID 2279128Notes

Reaction equation

HRID 2279128 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27]OS(C)(=O)=O)[CH:12]=2)=[CH:7][CH:6]=1.[CH3:33][CH:34]1[CH2:39][NH:38][C:37]([CH3:41])([CH3:40])[CH2:36][N:35]1[CH2:42][C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:16]=[C:15]3[N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[N:18]=[C:19]([CH3:20])[C:14]3=[C:13]([CH2:27][N:38]3[CH2:39][CH:34]([CH3:33])[N:35]([CH2:42][C:43]4[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=4)[CH2:36][C:37]3([CH3:40])[CH3:41])[CH:12]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 648390912,5,5-Trimethyl-1-(pyridin-3-ylmethyl)piperazineHCID 90014099Methanesulfonic acid 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester

Product 1

HCID 900135336-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-4-(2,2,5-trimethyl-4-pyridin-3-ylmethyl-piperazin-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridineYield 36.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 150 mg of methanesulfonic acid 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-ylmethyl ester, and 85 mg 2,5,5-trimethyl-1-(pyridin-3-ylmethyl)piperazine in 4 ml of dry THF were added 0.28 ml of DIPEA. The reaction was heated to 140° C. for 60 min in a microwave reactor. The reaction was diluted with ethyl acetate and water and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphaste, filtrated and concentrated. The resulting oil was purified by chromatography (silica, heptanes/ethyl acetate). 69 mg of the title compound were obtained.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphaste
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. customThe resulting oil was purified by chromatography (silica, heptanes/ethyl acetate)

Sources & evidence

ORD record
ord-02090e0ca12b4c9c86680228793a77b8
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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