Succinimide → HCID 66733058, compound

HRID 1966822Notes

Reaction equation

HRID 1966822 reaction equation
[CH:1]1([NH:7][C:8]2[C:13]([C:14]3[CH2:18][C:17]([CH2:21][CH2:22][OH:23])([CH2:19]O)[O:16][N:15]=3)=[CH:12][N:11]=[C:10]3[N:24]([CH2:27][CH3:28])[N:25]=[CH:26][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(=O)NC(=O)CC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH:1]1([NH:7][C:8]2[C:9]3[CH:26]=[N:25][N:24]([CH2:27][CH3:28])[C:10]=3[N:11]=[CH:12][C:13]=2[C:14]2[CH2:18][C:17]3([CH2:21][CH2:22][O:23][CH2:19]3)[O:16][N:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11439SuccinimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 25073835HCID 25073835, compound

Product 1

HCID 66733058HCID 66733058, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{3-[4-(Cyclohexylamino)-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl]-5-(hydroxymethyl)-4,5-dihydroisoxazol-5-yl}ethanol (150 mg, 0.00038 mole) (example 11), triphenylphosphine (132 mg, 0.00050 mole) and succinimide (42 mg, 0.00042 mole) were taken in dry tetrahydrofuran. Diisopropyl azodicarboxylate (0.115 ml, 0.00058 mole) was added dropwise. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The crude product obtained was purified by column chromatography.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-63acb5440a5f49258702eaa49d333668
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

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