Picolinic acid → HCID 57513840, 화합물

HRID 2368435노트

반응식

HRID 2368435 반응식
[NH2:1][C:2]([CH3:26])([CH3:25])[C:3]([NH:5][C:6]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:7]=1)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[C:57](O)=[O:58]>C(Cl)Cl.CCOC(C)=O>[CH2:18]([N:8]1[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:10][C:6]([NH:5][C:3]([C:2]([NH:1][C:57]([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][N:51]=2)=[O:58])([CH3:26])[CH3:25])=[O:4])=[N:7]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

6

반응물 3

HCID 1018Picolinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57513839HCID 57513839, 화합물

생성물 1

HCID 57513840HCID 57513840, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

2-Amino-N-[1-benzyl-5-(4-fluoro-phenyl)-1H-[1,2,4]triazol-3-yl]-2-methyl-propionamide (137 mg, 0.388 mmol), HATU (295 mg, 0.776 mmol), and picolinic acid (72 mg, 0.582 mmol) were stirred in DCM (6 mL). TEA (108 uL, 0.776 mmol) was added to the reaction mixture and it was stirred for 1 day. It was diluted with EtOAc (65 mL) and extracted with water (15 mL), followed by saturated NaHCO3 (15 mL). The organic layer was dried with a brine wash (10 mL) followed by Na2SO4. The solvents were removed in vacuo and the residue was purified by reverse phase HPLC (C18, 45-100% MeOH/H2O+5 mM NH4OH) followed by silica gel chromatography (0-30% ACN/DCM) to afford the title compound as a white solid: 1H NMR (400 MHz, DICHLOROMETHANE-d2) δ ppm 1.73 (s, 6H) 5.35 (s, 2H) 7.07-7.22 (m, 4H) 7.26-7.39 (m, 3H) 7.49 (ddd, J=7.61, 4.77, 1.14 Hz, 1H) 7.52-7.61 (m, 2H) 7.90 (td, J=7.74, 1.71 Hz, 1H) 8.19 (dt, J=7.77, 1.04 Hz, 1H) 8.47 (br. s., 1H) 8.58 (ddd, J=4.77, 1.61, 0.95 Hz, 1H) 9.45 (br. s., 1H); Rt (method A)=1.22 min, (M+H)+ 459.0.

후처리

  1. extractionextracted with water (15 mL)
  2. dry with materialThe organic layer was dried with a brine
  3. washwash (10 mL)
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by reverse phase HPLC (C18, 45-100% MeOH/H2O+5 mM NH4OH)

출처 및 근거

ORD 기록
ord-d6167d5f95024ffca43a989e78ad9521
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703761B2

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