Triethylamine → N-{5-Amino-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazin-6-yl}methanesulphonamide

HRID 2278854노트

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HRID 2278854 반응식
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:15]=[N:16][C:17]([NH2:21])=[C:18]([NH2:20])[N:19]=2)=[N:6]1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].C(N(CC)CC)C>ClCCl>[NH2:20][C:18]1[N:19]=[C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:22]=[CH:23][CH:24]=[CH:25][C:2]=3[F:1])[N:6]=2)[N:15]=[N:16][C:17]=1[NH:21][S:27]([CH3:26])(=[O:29])=[O:28]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 716216963-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazine-5,6-diamine

생성물 1

HCID 71621697N-{5-Amino-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazin-6-yl}methanesulphonamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

200 mg (0.595 mmol) of 3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazine-5,6-diamine were admixed with 8 ml of dichloromethane and cooled to 0° C. 545 mg (4.757 mmol) of methanesulphonyl chloride and 481 mg (4.757 mmol) of triethylamine were added and the mixture was stirred at RT for 72 h. The mixture was diluted with dichloromethane and the precipitate was filtered off with suction. The filtrate was partitioned between water and ethyl acetate. The organic phase was dried over sodium sulphate and concentrated on a rotary evaporator. The residue was purified by preparative HPLC (mobile phase: acetonitrile/water with 0.1% TFA, gradient 30:70→95:5). This gave 57 mg (18% of theory) of the target compound.

후처리

  1. filtrationthe precipitate was filtered off with suction
  2. customThe filtrate was partitioned between water and ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was purified by preparative HPLC (mobile phase: acetonitrile/water with 0.1% TFA, gradient 30:70→95:5)

출처 및 근거

ORD 기록
ord-a4d8777dc9984f2c9808400abbd95ce4
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133191B2

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