Phthalimide → 2-[(2S)-2-[2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-5-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 339995Notes

Reaction equation

HRID 339995 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:28])[C:6]=1[C:7]1[N:12]=[C:11]2[CH2:13][N:14]([C@@H:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)[CH2:18]O)[C:15](=[O:16])[C:10]2=[CH:9][CH:8]=1.[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:28])[C:6]=1[C:7]1[N:12]=[C:11]2[CH2:13][N:14]([C@@H:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=3)[CH2:18][N:33]3[C:29](=[O:39])[C:30]4[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:32]3=[O:34])[C:15](=[O:16])[C:10]2=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 866814812-(4-chloro-1-methyl-1H-pyrazol-5-yl)-6-[(1S)-1-(3-fluorobenzyl)-2-hydroxyethyl]-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

Product 1

HCID 866814822-[(2S)-2-[2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-5-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-3-(3-fluorophenyl)propyl]-1H-isoindole-1,3(2H)-dioneYield 23.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-chloro-1-methyl-1H-pyrazol-5-yl)-6-[(1S)-1-(3-fluorobenzyl)-2-hydroxyethyl]-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (0.065 g, 0.16 mmol) and phthalimide (0.029 g, 0.19 mmol) in tetrahydrofuran (5 mL) at 25° C. was added diethyl azodicarboxylate (0.096 mL, 0.24 mmol) and triphenylphosphine (0.055 g, 0.21 mmol). The reaction mixture was stirred at room temperature for 2 hr. After concentration, the residue was purified by pH=2 Prep.—HPLC to give 0.020 g (23% yield) of the desired product as white powder. LC/MS found: 530.1 (M+H)+.

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by pH=2 Prep.—HPLC

Sources & evidence

ORD record
ord-9b4973eb96f04d9b8242e32f5ab06124
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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