Acetic Acid → HCID 178491999、化合物

HRID 1244320ノート

反応式

HRID 1244320 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH:15][C:16]([C:18]1[NH:27][C:21]2=[N:22][C:23]([Cl:26])=[CH:24][CH:25]=[C:20]2[N:19]=1)=[S:17].Br.CC(O)=O.CS(C)=O.[OH-].[NH4+]>C(OCC)(=O)C.O>[Cl:26][C:23]1[N:22]=[C:21]2[NH:27][C:18]([C:16]3[S:17][C:5]4[C:6]([N:9]5[CH2:14][CH2:13][O:12][CH2:11][CH2:10]5)=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=4[N:15]=3)=[N:19][C:20]2=[CH:25][CH:24]=1

参加物

8

反応物 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 14923Ammonium HydroxideHCID 178492017HCID 178492017、化合物

生成物 1

HCID 178491999HCID 178491999、化合物収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

1.0 g 5-Chloro-3H-imidazo[4,5-b]pyridine-2-carbothioic acid (2-methoxy-5-morpholin-4-yl-phenyl)-amide (2.5 mmol) was dissolved in ethyl acetate (7 ml), heated to reflux and treated with 0.87 ml HBr in AcOH (5.7M, 5.0 mmol) and 0.2 ml DMSO (3.0 mmol). Stirring at reflux was continued for 2 h. Upon cooling a precipitation formed, which was isolated and dissolved in water (2 ml). The pH was adjusted to 10 with 25% ammonium hydroxide in water. Once again a precipitation formed, which was filtered. The residue on the filter was washed with water and dried in vacuo. One obtained 0.91 g 5-chloro-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridine (92%) as a yellow solid; M.p.: >300° C. (dec.).

後処理

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureat reflux
  4. temperatureUpon cooling
  5. customa precipitation
  6. customformed
  7. customwhich was isolated
  8. customOnce again a precipitation
  9. customformed
  10. filtrationwhich was filtered
  11. washThe residue on the filter was washed with water
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-a629c3db83e5413d8db1f8208afda737
出典データセット
uspto-grants-2006_10
特許番号
US07122545B2

反応ノート

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