Phthalimide → HCID 118214746, compound

HRID 2205605Notes

Reaction equation

HRID 2205605 reaction equation
O[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]3[N:25]([CH3:26])[CH:24]=[CH:23][C:10]3=[N:11][C:12]=2[C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH3:14])[CH2:3]1.[C:27]1(=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:36])[NH:28]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:37]=[C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:36])[N:28]1[CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]3[N:25]([CH3:26])[CH:24]=[CH:23][C:10]3=[N:11][C:12]=2[C@@H:13]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH3:14])[CH2:3]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 118214745HCID 118214745, compound

Product 1

HCID 118214746HCID 118214746, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl ((1S)-1-(6-(3-hydroxypyrrolidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (250 mg, 0.694 mmol), isoindoline-1,3-dione (153 mg, 1.04 mmol) and PPh3 (328 g, 1.25 mmol) in THF (2 mL) was stirred at 0° C. Next, diethyl azodicarboxylate (217 mg, 1.25 mmol) was added dropwise at 0° C. and the mixture was stirred at 20° C. for 16 hours. The solvent was evaporated in vacuo, and the residue was purified by preparative TLC to give the title compound as a white solid (200 mg, 42.3%). ESI-MS m/z [M+H]+ calc'd for C22H31N5O4, 490. found 490.

Workup

  1. stirringthe mixture was stirred at 20° C. for 16 hours
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-141101345c004fc2884e2b09a25aa883
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

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