Cesium carbonate → N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamide

HRID 626654

반응식

HRID 626654 반응식
Cl[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[CH:5]=[CH:4][N:3]=1.[CH:19]1([C:22]([NH2:24])=[O:23])[CH2:21][CH2:20]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+]>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]>[Cl:18][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]([Cl:17])[C:11]=1[N:9]1[CH:8]=[C:7]2[C:2]([NH:24][C:22]([CH:19]3[CH2:21][CH2:20]3)=[O:23])=[N:3][CH:4]=[CH:5][C:6]2=[N:10]1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866970364-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 69671224N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamide수율 35%

시약·촉매·용매 2

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

실험 절차

A suspension of 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (25 mg, 0.084 mmol), cyclopropanecarboxamide (16 mg, 0.19 mmol), Xantphos (14 mg, 0.024 mmol), Pd2(dba)3 (14 mg, 0.016 mmol) and Cs2CO3 (152 mg, 0.470 mmol) in dry dioxane (4.0 mL) was sealed in a microwave vial after degassing with nitrogen. The mixture was irradiated at 160° C. for 60 minutes in the microwave and then cooled to room temperature. The solid material was removed via filtration and the filtrate was purified via prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford N-(2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl)cyclopropanecarboxamide (10 mg, 35% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.19 (br, 1H), 8.90 (s, 1H), 7.99 (d, J=6.5 Hz, 1H), 7.79-7.67 (m, 3H), 7.39 (d, J=6.0 Hz, 1H), 2.13 (m, 1H), 0.92-0.86 (m, 4H). LCMS (Method A): RT=5.50 min, m/z: 347.0 [M+H+].

후처리

  1. customwas sealed in a microwave vial
  2. customafter degassing with nitrogen
  3. customThe mixture was irradiated at 160° C. for 60 minutes in the microwave
  4. customThe solid material was removed via filtration
  5. customthe filtrate was purified via 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-785056e2441a4315af3de8ec18e8ec64
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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