Phthalimide → HCID 118214741, compound

HRID 2205600Notes

Reaction equation

HRID 2205600 reaction equation
O[CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[C:10]3[N:26]([CH3:27])[CH:25]=[CH:24][C:11]3=[N:12][C:13]=2[C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15])[CH2:3]1.[C:28]1(=[O:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30](=[O:37])[NH:29]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:38]=[C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30](=[O:37])[N:29]1[CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[C:10]3[N:26]([CH3:27])[CH:25]=[CH:24][C:11]3=[N:12][C:13]=2[C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH3:15])[CH2:3]1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 118214742HCID 118214742, compound

Product 1

HCID 118214741HCID 118214741, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl ((1S)-1-(6-(3-hydroxypiperidin-1-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (300 mg, 0.802 mmol), isoindoline-1,3-dione (165 mg, 1.12 mmol) and PPh3 (377 g, 1.44 mmol) in THF (2 mL) was stirred at 0° C. Next, diethyl azodicarboxylate (251 mg, 1.44 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 (100 mg, 35.2%). ESI-MS m/z [M+H]+ calc'd for C28H33N5O4, 504. found 504.

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-501d880e8c7d4407a6c4428ea7a594c6
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

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