Sodium borohydride → 1-{6-[(6-Ethoxy-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea

HRID 517811ノート

反応式

HRID 517811 の反応式
[BH4-].[Na+].[CH2:3]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([S:15][C:16]3[CH:36]=[CH:35][C:19]4[N:20]=[C:21]([NH:23][C:24]([NH:26][CH2:27][CH2:28][N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[O:25])[S:22][C:18]=4[CH:17]=3)=[N:13][N:14]=2)[N:11]=1)[CH3:4]>C(O)C>[CH2:3]([O:5][C:6]1[CH2:7][CH2:8][C:9]2[N:10]([C:12]([S:15][C:16]3[CH:36]=[CH:35][C:19]4[N:20]=[C:21]([NH:23][C:24]([NH:26][CH2:27][CH2:28][N:29]5[CH2:30][CH2:31][O:32][CH2:33][CH2:34]5)=[O:25])[S:22][C:18]=4[CH:17]=3)=[N:13][N:14]=2)[N:11]=1)[CH3:4]

参加物

4

反応物 2

HCID 4311764Sodium borohydride2 回HCID 425986581-{6-[(6-Ethoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea

生成物 1

HCID 425986591-{6-[(6-Ethoxy-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea収率 40.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

27 mg of sodium borohydride are added to a mixture of 179 mg of 1-{6-[(6-ethoxy[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea in 10 cm3 of ethanol. The reaction is refluxed for 3.5 h, and then 108 mg of sodium borohydride are added gradually and the reflux is maintained for 48 h. The reaction mixture is concentrated to dryness under reduced pressure. The residue is purified by chromatography on Biotage Quad 12/25 (KP-SIL, 60 A; 32-63 mM), elution being carried out with a dichloromethane/methanol gradient of 99/1 to 93/7. 72 mg of 1-{6-[(6-ethoxy-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazin-3-yl)sulphanyl]-1,3-benzothiazol-2-yl}-3-[2-(morpholin-4-yl)ethyl]urea are thus obtained in the form of a white powder, the characteristics of which are as follows:

後処理

  1. temperatureThe reaction is refluxed for 3.5 h
  2. temperaturethe reflux is maintained for 48 h
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  4. customThe residue is purified by chromatography on Biotage Quad 12/25 (KP-SIL, 60 A
  5. wash32-63 mM), elution

出典と根拠

ORDレコード
ord-5aee6e30b413414e9bc4241d23144dc9
出典データセット
uspto-grants-2015_08
特許番号
US09115134B2

反応ノート

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