1,2-Dichloroethane → N-(2-hydroxyethyl)-6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamide

HRID 58108노트

반응식

HRID 58108 반응식
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][NH:15]2.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH2:38][CH2:39][CH2:40][OH:41].C(N(C(C)C)C(C)C)C>CN(C=O)C.CCOC(C)=O>[OH:41][CH2:40][CH2:39][NH:38][C:8](=[O:10])[C:6]1[CH:5]=[CH:4][C:3]([C:11]2[CH:19]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[C:2]([CH3:1])[N:7]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 897833556-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid

생성물 1

HCID 89782824N-(2-hydroxyethyl)-6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamide수율 36.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To 6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid (1.6 g, 4.98 mmol) in DMF (20 mL) were added HOBt (0.942 g, 6.97 mmol), EDC (1.432 g, 7.47 mmol), 2-aminoethanol (0.913 g, 14.94 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (4.34 mL, 24.90 mmol). The reaction mixture was stirred for 16 hours at room temperature, was subsequently diluted with EtOAc and was washed with brine. Volatiles were evaporated from the organic phase and the residue was purified by CombiFlash® chromatography, eluting with a gradient of 0-20% MeOH in DCM. The product-containing fractions were combined and concentrated in vacuo to give the title compound as a white solid (0.658 g, 36.3%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.43 (s, 3H), 3.44 (q, J=5.98 Hz, 2H), 3.57 (t, J=5.94 Hz, 2H), 7.38-7.44 (m, 1H), 7.90-8.07 (m, 4H), 8.70 (t, J=5.81 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C17H15F3N4O2, 365.1. found 365.2.

후처리

  1. washwas washed with brine
  2. customVolatiles were evaporated from the organic phase
  3. customthe residue was purified by CombiFlash® chromatography
  4. washeluting with a gradient of 0-20% MeOH in DCM
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d8e84ccb75fa4262a6068ee19592e58f
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434743B2

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