Phthalimide → 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

HRID 550497Notes

Reaction equation

HRID 550497 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]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.[C:30]1(=[O:40])[NH:34][C:33](=[O:35])[C:32]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:31]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1.CN(C=O)C>[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:34]4[C:30](=[O:40])[C:31]5[C:32](=[CH:36][CH:37]=[CH:38][CH:39]=5)[C:33]4=[O:35])[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

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 116759782-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethanol

Product 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)-dioneYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethanol (prepared as described in Example 4/500 mg, 1.21 mmol), phthalimide (534 mg, 3.63 mmol) and triphenylphosphine were dissolved in a 1:1 mixture of THF and DMF (10 ml). Ditertbutyl azodicarboxylate (698 mg, 3.03 mmol) was added at 0° C. and mixture was stirred at room temperature for 4 hours. After evaporation, the crude mixture was purified by silica gel chromatography (6% methanol/CH2Cl2) to give the title compound (33% yield); NMR Spectrum: 4.09 (t, 2H), 4.50 (t, 2H), 5.31 (s, 2H), 7.31 (d, 1H), 7.38 (t, 1H), 7.60 (d, 1H), 7.77 (dd, 1H), 7.83-7.90 (m, 4H), 7.99 (s, 1H), 8.05 (d, 1H), 8.31 (s, 1H), 8.61 (d, 1H); Mass Spectrum: 542 (MH+).

Workup

  1. customAfter evaporation
  2. customthe crude mixture was purified by silica gel chromatography (6% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-748fa867ca674348aa862ff2f2b4ec5b
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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