Cesium carbonate → HCID 59618307, 화합물

HRID 449932노트

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HRID 449932 반응식
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4]([NH:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9](Cl)[CH:8]=1)=[O:5].[CH:21]1([C:24]([NH2:26])=[O:25])[CH2:23][CH2:22]1.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.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].O1CCOCC1>[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4]([NH:6][C:7]1[C:12]([F:13])=[CH:11][N:10]=[C:9]([NH:26][C:24]([CH:21]2[CH2:23][CH2:22]2)=[O:25])[CH:8]=1)=[O:5]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86648966HCID 86648966, 화합물

생성물 1

HCID 59618307HCID 59618307, 화합물수율 9.3%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

To a microwave tube was added 2,4,6-trichloro-N-(2-chloro-5-fluoropyridin-4-yl)benzamide (71 mg, 0.20 mmol), cyclopropanecarboxamide (42.8 mg, 0.50 mmol), Pd2(dba)3 (18 mg, 0.020 mmol), XantPhos (14 mg, 0.025 mmol), Cs2CO3 (197 mg, 0.60 mmol) and dioxane (1.5 mL). The mixture was degassed with N2 for 2 min. The resulting mixture was irradiated in a microwave reactor at 140° C. for 35 min and then cooled to room temperature. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired product (7.5 mg, yield: 9.2%). 1H NMR (DMSO-d6, 400 MHz): δ 11.08 (s, 1H), 10.83 (d, 1H), 9.00 (s, 1H), 8.32 (s, 1H), 7.82 (s, 2H), 1.98 (d, J=4.6 Hz, 1H), 0.82 (t, J=6.1 Hz, 4H). LCMS (ESI) m/z: 402.0 [M+H+].

후처리

  1. customThe mixture was degassed with N2 for 2 min
  2. customThe resulting mixture was irradiated in a microwave reactor at 140° C. for 35 min
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min)

출처 및 근거

ORD 기록
ord-239efe90061c4774a957d551ba9395e9
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486950B2

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