Benzocaine → HCID 59618316, 화합물

HRID 449937노트

반응식

HRID 449937 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 59618316HCID 59618316, 화합물수율 65%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
130 °C

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-5c1cbb433ac84d27a8cf45a2761044e6
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486950B2

반응 노트

불러오는 중…