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

HRID 1891983ノート

反応式

HRID 1891983 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3befd8ab08c74fc182ae418331f3d49e
出典データセット
uspto-grants-2013_08
特許番号
US08507530B2

反応ノート

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