Benzocaine → HCID 59618316、化合物

HRID 449937ノート

反応式

HRID 449937 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 59618316HCID 59618316、化合物収率 65%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
130 °C

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-5c1cbb433ac84d27a8cf45a2761044e6
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

反応ノート

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