Formaldehyde → (3-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-yl)-dimethyl-amine

HRID 78277노트

반응식

HRID 78277 반응식
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3C(N)=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.N1C=CC=CC=1C.B.FC(F)(F)C(O)=O.[CH3:45][N:46]([CH3:49])[CH:47]=O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][C:14]2[CH:18]=[C:17]([C:19]3[C:47]([N:46]([CH3:49])[CH3:45])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 160615083-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamineHCID 16217944Borane;2-methylpyridine

생성물 1

HCID 59255259(3-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-yl)-dimethyl-amine수율 21%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a mixture of 3-(3-(4-benzyloxy-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine (50 mg, 0.14 mmol) described in Example 1 and N,N-dimethylformamide (0.5 mL) were added a formaldehyde aqueous solution (34 mg, 0.42 mmol, content: 37%), α-picoline-borane (37 mg, 0.35 mmol), and acetic acid (50 μL), which was stirred overnight at the same temperature. Trifluoroacetic acid (50 μL) was added to the reaction mixture, which was stirred for 30 minutes at room temperature. The solvent was evaporated under a reduced pressure, and the residue thus obtained was purified by reverse-phase high performance liquid chromatography (using an acetonitrile-water mobile phase containing 0.1% trifluoroacetic acid) to obtain the title compound (15 mg, 21%) as a trifluoroacetate.

후처리

  1. stirringwas stirred for 30 minutes at room temperature
  2. customThe solvent was evaporated under a reduced pressure
  3. customthe residue thus obtained
  4. customwas purified by reverse-phase high performance liquid chromatography (
  5. additioncontaining 0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-148d55597a2b48f19b18e173d7c709b1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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