Diisopropylethylamine → 2,6-dichloro-N-(2-((1R,2R)-2-chlorocyclopropanecarboxamido)pyridin-4-yl)benzamide

HRID 449908노트

반응식

HRID 449908 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([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:5]=[CH:4][N:3]=1.[Cl:19][CH:20]1[CH2:22][CH:21]1[C:23](O)=[O:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:17])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:23]([C@H:21]2[CH2:22][C@H:20]2[Cl:19])=[O:24])[CH:7]=1)=[O:18]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 133995232-Chlorocyclopropane-1-carboxylic acidHCID 59618313N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide

생성물 1

HCID 596180252,6-dichloro-N-(2-((1R,2R)-2-chlorocyclopropanecarboxamido)pyridin-4-yl)benzamide수율 12%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

To a solution of N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (150 mg, 0.54 mmol), 2-chlorocyclopropanecarboxylic acid (66 mg, 0.54 mmol) and HATU (381 mg, 1.08 mmol) in dry DMF (4.5 mL) was added DIPEA (144 mg, 1.08 mmol). The mixture was stirred at 110° C. in a microwave reactor for 1 hour. The mixture was cooled to room temperature and diluted with EtOAc (30 mL). The organic solution was washed with water (10 mL) and brine (10 mL), dried over Na2SO4 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 compounds.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. washThe organic solution was washed with water (10 mL) and brine (10 mL)
  3. dry with materialdried over Na2SO4
  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-0b50e7736efd4c7bac27045464ccb921
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486950B2

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