Triphenylphosphine → HCID 22036430, compound

HRID 991637Notes

Reaction equation

HRID 991637 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. filtrationThe mixture was filtered
  2. customto remove the resin
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica

Sources & evidence

ORD record
ord-fe03ca04cce84aafa76f2ed9322c39d3
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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