Triphenylphosphine → HCID 22036430, compound

HRID 493292Notes

Reaction equation

HRID 493292 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:27]([O:32][CH2:33][CH2:34][OH:35])=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].O[C:37]1[C:45]2[C:41](=[N:42][S:43][N:44]=2)[CH:40]=[CH:39][CH:38]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>>[N:42]1[S:43][N:44]=[C:45]2[C:37]([O:35][CH2:34][CH2:33][O:32][C:27]3[C:26]([N:23]4[CH2:24][CH2:25][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:21][CH2:22]4)=[N:31][CH:30]=[CH:29][N:28]=3)=[CH:38][CH:39]=[CH:40][C:41]=12

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 49146732,1,3-Benzothiadiazol-4-olHCID 5462977Diethyl azodicarboxylateHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 22036430HCID 22036430, compoundYield 12%

Procedure

DEAD (0.52 mL, 3.3 mmol) was added to a slurry of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (1.00 g, 3.08 mmol; prepared in Example 52, Step 2), 4-hydroxy-2,1,3-benzothiadiazole* (0 46 g, 3.0 mmol) and resin bound PPh3 (1.1 g. 3.3 mmol) and shaken until HPLC showed no starting material The mixture was filtered to remove the resin, concentrated and purified by column chromatography on silica to give 0.163 g (12%) of the title compound. Pos-EI-MS shows M+ and 11 ions supporting the stated structure HRMS m/z calcd for C21H26N6O4S (M)+ 458 1736. found 458.1716.

Workup

  1. filtrationwas filtered
  2. customto remove the resin
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica

Sources & evidence

ORD record
ord-c1fffc96db2a4658ac07ea6f8d2ea3f2
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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