Triphenylphosphine → N-(5-Chloropyridin-2-yl)-2-[2-(1,4-dioxaspiro[4.5]dec-8-yloxy)-4-isopropyl-benzoylamino]benzamide

HRID 644214Notes

Reaction equation

HRID 644214 reaction equation
[CH:1]1([O:11][C:4]2([CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]2)[O:3]1)[CH3:2].[CH:12]([C:15]1[CH:39]=[CH:38][C:18]([C:19]([NH:21][C:22]2[CH:37]=[CH:36][CH:35]=[CH:34][C:23]=2[C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=2)=[O:25])=[O:20])=[C:17](O)[CH:16]=1)([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CCOCC.CN(C=O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([NH:26][C:24](=[O:25])[C:23]2[CH:34]=[CH:35][CH:36]=[CH:37][C:22]=2[NH:21][C:19](=[O:20])[C:18]2[CH:17]=[CH:16][C:15]([CH:12]([CH3:14])[CH3:13])=[CH:39][C:38]=2[O:10][CH:7]2[CH2:8][CH2:9][C:4]3([O:3][CH2:2][CH2:1][O:11]3)[CH2:5][CH2:6]2)=[N:28][CH:29]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 685329372-[2-Hydroxy-4-isopropylbenzoylamino]-N-(5-chloropyridin-2-yl)benzamideHCID 866342054-Hydroxycyclohexanone-1,1-ethylene ketal

Product 1

HCID 68535594N-(5-Chloropyridin-2-yl)-2-[2-(1,4-dioxaspiro[4.5]dec-8-yloxy)-4-isopropyl-benzoylamino]benzamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Hydroxycyclohexanone-1,1-ethylene ketal (0.63 g, 4 mmol), 2-[4-isopropyl-2-hydroxybenzoylamino]-N-(5-chloropyridin-2-yl)benzamide (1.64 g, 4 mmol), triphenyl-phosphine (1.05 g, 4 mmol), and dry DMF (2 mL) were sonicated for 5 min at room temperature. DIAD (0.8 mL, 4 mmol) was added and sonication was continued for 1 h. Ether (40 mL) was added and the solution was chilled overnight in the freezer to crystallize triphenylphosphine oxide. The crystals were filtered, washed with a little ether, and the combined filtrates were evaporated to dryness to give a yellow oil.

Workup

  1. customsonication
  2. temperaturethe solution was chilled overnight in the freezer
  3. customto crystallize triphenylphosphine oxide
  4. filtrationThe crystals were filtered
  5. washwashed with a little ether
  6. customthe combined filtrates were evaporated to dryness
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-b9f22882edd84b7f8dc364acfd1a4f4b
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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