1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 178473881, compound

HRID 513270Notes

Reaction equation

HRID 513270 reaction equation
Cl[C:2]1[CH:10]=[C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14][CH2:13]2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1.O.O.O.[O-]C1C=CC=CC=1.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:32]([N:29]1[CH2:28][CH2:27][N:26]([C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:2]3[CH:10]=[C:9]([NH:11][C@H:12]4[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14][CH2:13]4)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=3)=[CH:21][CH:22]=2)[CH2:31][CH2:30]1)(=[O:34])[CH3:33]

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 23681143Sodium Phenoxide TrihydrateHCID 178513743HCID 178513743, compound

Product 1

HCID 178473881HCID 178473881, compoundYield 12.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-chloro-4-((cis)-4-hydroxycyclohexylamino)nicotinamide (65 mg, 0.240 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (60 mg, 0.273 mmol), sodium phenoxide trihydrate (100 mg, 0.588 mmol), xantphos (30 mg, 0.051 mmol) and Pd2dba3 (20 mg, 0.021 mmol) in dioxane (3 mL) was degassed with Ar, then was stirred at 120 C for 18 h. HOAc (1 mL) was added. The mixture was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (14 mg). MS 453.5 (M+H); UV 202.9, 259.0 nm; t 0.380 min.

Workup

  1. customwas degassed with Ar
  2. additionHOAc (1 mL) was added
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-3fd9f7b473a64d13ac19fd311392d33a
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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