Triphenylphosphine → HCID 66961316, compound

HRID 69007Notes

Reaction equation

HRID 69007 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[OH:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][CH:46]=1)[C:43](=[O:47])[NH:42][CH:41]=[CH:40]2.[N:48]1[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54][CH2:55][N:56]([CH2:61][C:62]2[CH:67]=[CH:66][N:65]=[CH:64][CH:63]=2)[CH2:57][CH2:58][CH2:59]O)[CH:49]=1.C(OC(=O)C)C.[ClH:74]>C(OCC)(=O)C.O1CCCC1>[ClH:74].[ClH:74].[ClH:74].[N:48]1[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54][CH2:55][N:56]([CH2:61][C:62]2[CH:63]=[CH:64][N:65]=[CH:66][CH:67]=2)[CH2:57][CH2:58][CH2:59][O:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[C:43](=[O:47])[NH:42][CH:41]=[CH:40]3)[CH:49]=1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 105111706-hydroxyisoquinolin-1(2H)-oneHCID 21866389Hydrogen chloride-ethyl acetateHCID 669609373-[(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol

Product 1

HCID 66961316HCID 66961316, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triphenyl phosphine (51 mg) and di-tert-butyl azodicarboxylate (45 mg) were added to a tetrahydrofuran (THF) solution (1.5 ml) of 6-hydroxy-2H-isoquinolin-1-one (29 mg), and 3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol (40 mg). The mixture was stirred overnight. After the reaction mixture was condensed under reduced pressure, the residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=1:0→4:1). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution (0.06 ml) was added to an ethyl acetate solution of the residue, which was stirred at room temperature for 30 minutes. The generated insoluble matter was separated by filtration, and was dried to produce the title compound (31.4 mg) as a white powder.

Workup

  1. customcondensed under reduced pressure
  2. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=1:0→4:1)
  3. customcondensed under reduced pressure
  4. stirringwas stirred at room temperature for 30 minutes
  5. customThe generated insoluble matter was separated by filtration
  6. customwas dried

Sources & evidence

ORD record
ord-c0ad8bb8176545f9b34b0cc3b92a29b2
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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