Hydrazine hydrate (1:1) → 3-(2-aminoethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 550498Notes

Reaction equation

HRID 550498 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]3[NH:23][N:24]=[C:25]([O:26][CH2:27][CH2:28][N:29]4C(=O)C5C(=CC=CC=5)C4=O)[C:18]=23)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.O.NN>C(O)C>[NH2:29][CH2:28][CH2:27][O:26][C:25]1[C:18]2[C:19](=[N:20][CH:21]=[N:22][C:17]=2[NH:16][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)=[C:2]([Cl:1])[CH:3]=2)[NH:23][N:24]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 116995282-{2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 115388303-(2-aminoethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-{2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}-1H-isoindole-1,3(2H)-dione (prepared as described in Example 90/350 mg, 0.65 mmol) and hydrazine monohydrate (63111) in ethanol (2 ml) was refluxed overnight. After evaporation of the solvent, the crude material was purified by preparative HPLC (column beta-basic, Hypercil 5 μm, 21×100 mm) eluting with a mixture of water and acetonitrile containing 2g/l of ammonium carbonate (gradient) to give the title compound (184 mg, 69%); NMR Spectrum: 2.94 (t, 2H), 4.25 (t, 2H), 5.29 (s, 2H), 7.23 (d, 1H), 7.37 (t, 1H), 7.53-7.58 (m, 2H), 7.85-7.90 (m, 2H), 8.26 (s, 1H), 8.60 (br s, 2H). Mass Spectrum: 412 (MH+).

Workup

  1. temperaturewas refluxed overnight
  2. customAfter evaporation of the solvent
  3. customthe crude material was purified by preparative HPLC (column beta-basic, Hypercil 5 μm, 21×100 mm)
  4. washeluting with a mixture of water and acetonitrile containing 2g/l of ammonium carbonate (gradient)

Sources & evidence

ORD record
ord-266b0ae1d2fa4d6783ebb9e044f6cacb
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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