Benzocaine → HCID 59618316, compound

HRID 449937Notes

Reaction equation

HRID 449937 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[CH:3]=1.[NH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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]>[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=1[C:9]([NH:8][C:4]1[N:5]=[CH:6][N:7]=[C:2]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=2)[CH:3]=1)=[O:18]

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86648969HCID 86648969, compound

Product 1

HCID 59618316HCID 59618316, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
130 °C

Procedure

A mixture of N-(6-chloropyrimidin-4-yl)-2,6-dichlorobenzamide (302 mg, 1.0 mmol), ethyl 4-aminobenzoate (0.33 g, 2.0 mmol), Pd2(dba)3 (0.1 mmole, 92 mg), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (0.15 mmol, 87 mg) and cesium carbonate (2.0 mmoles; 652 mg) in a microwave tube was evacuated, back-filled with N2 (2×). 1,4-Dioxane (10 mL) was then added. The tube was sealed, and heated at 130° C. in microwave for 15 min. The mixture was filtered through Celite using EtOAc to rinse. The combined filtrates were concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% EtOAc/hexane) to afford ethyl 4-(6-(2,6-dichlorobenzamido)pyrimidin-4-ylamino)benzoate as an off-white solid (0.279 g, yield: 65%). LCMS (ESI) m/z: 431.0 [M+H+].

Workup

  1. customwas evacuated
  2. additionback-filled with N2 (2×)
  3. addition1,4-Dioxane (10 mL) was then added
  4. customThe tube was sealed
  5. filtrationThe mixture was filtered through Celite
  6. washto rinse
  7. concentrationThe combined filtrates were concentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (0-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-5c1cbb433ac84d27a8cf45a2761044e6
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

Loading…