Lithium Hydroxide → HCID 44626390、化合物

HRID 1951649

反応式

HRID 1951649 の反応式
[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[CH:6][N:5]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[C:4]=2[C:3]=1[C:21](O)=[O:22].C[O:25][C:26](=[O:37])[C:27]1[CH:32]=[CH:31][C:30]([C:33]2([NH2:36])[CH2:35][CH2:34]2)=[CH:29][CH:28]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N(CC)(CCC)CCC.[Li+].[OH-]>CN(C=O)C.O.C1COCC1.CO.CC(O)=O>[CH3:1][C:2]1[S:9][C:8]2[CH:7]=[CH:6][N:5]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=3)[C:4]=2[C:3]=1[C:21]([NH:36][C:33]1([C:30]2[CH:31]=[CH:32][C:27]([C:26]([OH:37])=[O:25])=[CH:28][CH:29]=2)[CH2:35][CH2:34]1)=[O:22]

参加物

10

反応物 5

HCID 3939Lithium HydroxideHCID 519799N,N-DipropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45140209Methyl 4-(1-aminocyclopropyl)benzoateHCID 67182624HCID 67182624、化合物

生成物 1

HCID 44626390HCID 44626390、化合物収率 56.7%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

A mixture of 0.3 g of 2-methyl-4-(4-trifluoromethyl-benzyl)-4H-thieno[3,2-b]pyrrole-3-carboxylic acid, 0.25 g of 4-(1-amino-cyclopropyl)-benzoic acid methyl ester, 0.5 g of HATU and 0.25 ml of Pr2NEt in 8 ml of DMF was stirred at room temperature for 16 h. The reaction was then diluted with 30 ml of water and extracted with 100 ml of EtOAc. The organic layer was washed with 50 ml of water and 50 ml of brine and dried over Na2SO4. The extract was filtered, and concentrated to give the crude methyl ester which was dissolved in 20 ml of 1:1 THF/MeOH and treated with 10 ml of 0.5 M aqueous LiOH solution. After stirring for 15 h at room temperature, 1 ml of AcOH was added and the reaction mixture was extracted with 75 ml of EtOAc. The organic layer was washed with 50 ml of brine, dried over Na2SO4. The extract was filtered and concentrated to give 0.25 g of the title compound as a light brown solid.

後処理

  1. extractionextracted with 100 ml of EtOAc
  2. washThe organic layer was washed with 50 ml of water and 50 ml of brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe extract was filtered
  5. concentrationconcentrated
  6. customto give the crude methyl ester which
  7. stirringAfter stirring for 15 h at room temperature
  8. extractionthe reaction mixture was extracted with 75 ml of EtOAc
  9. washThe organic layer was washed with 50 ml of brine
  10. dry with materialdried over Na2SO4
  11. filtrationThe extract was filtered
  12. concentrationconcentrated

出典と根拠

ORDレコード
ord-f8beb82efb4e4c018d8ed0a53d376f10
出典データセット
uspto-grants-2013_03
特許番号
US08404736B2

関連ノート

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