Methanol → HCID 69187894、化合物

HRID 1020274ノート

反応式

HRID 1020274 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:14][N:13]=[C:12]([CH2:15][NH:16][CH3:17])[N:11]=1)=[O:8].CO.[CH3:23][C:24]1[C:28]([CH:29]=O)=[C:27]([CH3:31])[O:26][N:25]=1.C([BH3-])#N.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:23][C:24]1[C:28]([CH2:29][N:16]([CH2:15][C:12]2[N:11]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]3[CH:18]=[CH:19][CH:20]=[C:2]([F:1])[CH:3]=3)=[O:8])[S:14][N:13]=2)[CH3:17])=[C:27]([CH3:31])[O:26][N:25]=1

参加物

7

反応物 4

HCID 887MethanolHCID 2895763,5-Dimethyl-4-Isoxazolecarbaldehyde2 回HCID 5003444Sodium cyanoborohydride2 回HCID 58055092HCID 58055092、化合物2 回

生成物 1

HCID 69187894HCID 69187894、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 6344Dichloromethane溶媒

実験手順

1-(3-Fluoro-benzyl)-3-(3-methylaminomethyl-[1,2,4]thiadiazol-5-yl)-urea (Intermediate XXVII) was taken up in DCM and methanol with 3,5-Dimethyl-isoxazole-4-carbaldehyde (2 eq.) and acetic acid (several drops). Reaction was stirred for several hours at ambient temperature. Sodium cyanoborohydride (2 eq.) was added at once and the reaction was stirred overnight at ambient temperature. An additional equivalent of 3,5-Dimethyl-isoxazole-4-carbaldehyde and sodium cyanoborohydride (2 eq.) was added and stirred 4 more hours. Crude r×n mixture was loaded directly onto a silica plug and eluted with 10% saturated NH3/MeOH in DCM. Purified by column chromatography (silica, DCM, 0-10% MeOH saturated with NH3) to give the title compound. 1H NMR (400 MHz, DMSO): 11.45 (br s, 1H), 7.43-7.35 (m, 2H), 7.17-7.05 (m, 3H), 4.38 (d, 2H), 3.58 (s, 2H), 3.33 (s, 2H), 2.31 (s, 3H), 2.16 (s, 3H), 2.15 (s, 3H).

後処理

  1. customReaction
  2. stirringwas stirred overnight at ambient temperature
  3. stirringstirred 4 more hours
  4. washeluted with 10% saturated NH3/MeOH in DCM
  5. customPurified by column chromatography (silica, DCM, 0-10% MeOH saturated with NH3)

出典と根拠

ORDレコード
ord-81710926290a45569c2e8327ca1ed29d
出典データセット
uspto-grants-2014_05
特許番号
US08716320B2

反応ノート

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