Phthalimide → HCID 58190566, compound

HRID 1892360Notes

Reaction equation

HRID 1892360 reaction equation
O[CH2:2][CH2:3][O:4]/[N:5]=[C:6](/[C:8]1[N:13]=[C:12]2[N:14]([CH2:17][C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][CH:22]=[CH:21]4)[N:15]=[N:16][C:11]2=[N:10][CH:9]=1)\[CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:47]1(=[O:57])[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:49](=[O:56])[NH:48]1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>C1COCC1>[N:24]1[C:25]2[C:20](=[CH:19][C:18]([CH2:17][N:14]3[C:12]4=[N:13][C:8](/[C:6](=[N:5]/[O:4][CH2:3][CH2:2][N:48]5[C:49](=[O:56])[C:50]6[C:55](=[CH:54][CH:53]=[CH:52][CH:51]=6)[C:47]5=[O:57])/[CH3:7])=[CH:9][N:10]=[C:11]4[N:16]=[N:15]3)=[CH:27][CH:26]=2)[CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58190498HCID 58190498, compound

Product 1

HCID 58190566HCID 58190566, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone O-2-hydroxyethyl oxime (example 23) (200 mg, 0.55 mmol) in THF (10 mL) were added triphenylphosphine (144 mg, 0.55 mmol), isoindoline-1,3-dione (81 mg, 0.55 mmol) and (E)-diisopropyl diazene-1,2-dicarboxylate (111 mg, 0.55 mmol) sequentially. The mixture was stirred at rt for 48 h and concentrated in vacuo. The residue was purified by column chromatography to afford 120 mg (42%) of the title compound. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.90 (s, 1H), 8.89 (m, 1H), 8.35 (d, 1H), 8.02 (m, 2H), 7.81 (d, 1H), 7.71 (m, 2H), 7.63 (m, 2H), 7.52 (dd, 1H), 6.19 (s, 2H), 4.53 (t, 2H), 3.97 (t, 2H), 2.20 (s, 3H). LCMS (method B): [MH]+=493, tR=2.52 min.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e27589ff5fb74e88b20c7d4b902f2ea3
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

Loading…