2-Amino-5-fluoropyridine → rac-cis-(2-(((5-Fluoropyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

HRID 60846

반응식

HRID 60846 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]([N:16]2[CH2:21][CH2:20][CH2:19][C@H:18]([CH3:22])[C@@H:17]2[CH:23]=O)=[O:15])=[CH:4][CH:3]=1.[F:25][C:26]1[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+]>[F:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][CH2:23][C@H:17]2[C@@H:18]([CH3:22])[CH2:19][CH2:20][CH2:21][N:16]2[C:14]([C:9]2[N:10]=[C:11]([CH3:13])[S:12][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:15])=[N:30][CH:31]=1

참가 물질

7

반응물 3

HCID 27377012-Amino-5-fluoropyridineHCID 5003444Sodium cyanoborohydrideHCID 131737135rac-cis-1-(5-(4-Fluorophenyl)-2-methylthiazole-4-carbonyl)-3-methylpiperidine-2-carbaldehyde

생성물 1

HCID 131737136rac-cis-(2-(((5-Fluoropyridin-2-yl)amino)methyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone

시약·촉매·용매 3

HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매HCID 10129899Acetic acid methanol용매

실험 절차

To a stirred solution of rac-cis-1-(5-(4-fluorophenyl)-2-methylthiazole-4-carbonyl)-3-methylpiperidine-2-carbaldehyde and 5-fluoropyridin-2-amine in methanol/acetic acid (50:1) was added sodium cyanoborohydride at 0° C. The reaction was then stirred at rt overnight. After ˜16 h, the reaction mixture was transferred to a seperatory funnel, diluted with EtOAc, saturated NaHCO3 and the layers separated. The organic layer was washed with water, brine, dried (MgSO4), and concentrated in vacuo. The crude reaction mixture was purified by reverse-phase preparative HPLC to afford the title compound. MS (ESI) 443.2 (M+H).

후처리

  1. waitAfter ˜16 h
  2. customthe reaction mixture was transferred to a seperatory funnel
  3. customthe layers separated
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction mixture
  8. customwas purified by reverse-phase preparative HPLC

출처 및 근거

ORD 기록
ord-dbdb52e682a049b0969c0e448bb73064
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440982B2

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