Acetic Acid → 2-(4'-((3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)biphenyl-4-yl)pyridazin-3(2H)-one

HRID 912488

反応式

HRID 912488 の反応式
[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:24][CH2:23][C@@H:22]5[CH2:25][N:26](C(OCC)=O)[CH2:27][C@H:21]45)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[N:6]=[CH:5][CH:4]=[CH:3]1.C(O)(=O)C>Br.CO>[N:20]1([C:17]2[CH:18]=[CH:19][C:14]([C:11]3[CH:12]=[CH:13][C:8]([N:7]4[C:2](=[O:1])[CH:3]=[CH:4][CH:5]=[N:6]4)=[CH:9][CH:10]=3)=[CH:15][CH:16]=2)[CH2:24][CH2:23][C@@H:22]2[CH2:25][NH:26][CH2:27][C@H:21]12

参加物

5

反応物 2

HCID 176Acetic AcidHCID 67396526(3aR,6aR)-ethyl 1-(4'-(6-oxopyridazin-1(6H)-yl)biphenyl-4-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

生成物 1

HCID 673963272-(4'-((3aR,6aR)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)biphenyl-4-yl)pyridazin-3(2H)-one収率 116.1%

試薬・触媒・溶媒 2

HCID 260Hydrogen Bromide溶媒HCID 887Methanol溶媒

反応条件

温度
67.5 °C

実験手順

A mixture of the product of Example 1E (7.50 g, 17.42 mmol) in 33% HBr in acetic acid (37 mL, 205.57 mmol, 11.8 equivalents) was heated to 65-70° C. for at least 6 hours while monitored by HPLC analysis for completion. When reaction is complete, the mixture is cooled to not more than 45° C. and is diluted with MeOH (111 mL). The mixture was cooled to 20-25° C., the product is collected by filtration and is washed with fresh MeOH (50 mL). The wet cake is dried in the vacuum oven at not more than 55° C. to provide the title compound (7.25 g, 94.8%).

後処理

  1. customWhen reaction
  2. temperaturethe mixture is cooled to not more than 45° C.
  3. temperatureThe mixture was cooled to 20-25° C.
  4. filtrationthe product is collected by filtration
  5. washis washed with fresh MeOH (50 mL)
  6. customThe wet cake is dried in the vacuum oven at not more than 55° C.

出典と根拠

ORDレコード
ord-65544bca844e4db5a601019f5e484df9
出典データセット
uspto-grants-2011_09
特許番号
US08026240B2

関連ノート

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