Diisopropylethylamine → N-(4-Aminothiophen-3-yl)-4-[1-(2-dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzamide

HRID 217642ノート

反応式

HRID 217642 の反応式
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][CH:5]([NH:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[CH2:24][CH2:23][CH2:22]2)=[O:17])[C:6]1[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][CH:7]=1.Cl.Cl.[NH2:31][C:32]1[C:36]([NH2:37])=[CH:35][S:34][CH:33]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[NH2:37][C:36]1[C:32]([NH:31][C:10](=[O:11])[C:9]2[CH:8]=[CH:7][C:6]([CH:5]([NH:15][C:16]([NH:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[CH2:24][CH2:23][CH2:22]4)=[O:17])[CH2:4][CH2:3][N:2]([CH3:28])[CH3:1])=[CH:14][CH:13]=2)=[CH:33][S:34][CH:35]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 127073423,4-Diaminothiophene dihydrochlorideHCID 670498974-[1-(2-Dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzoic acid

生成物 1

HCID 67049894N-(4-Aminothiophen-3-yl)-4-[1-(2-dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzamide収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-[1-(2-dimethylaminoethyl)-3-(indan-5-yl)ureidomethyl]benzoic acid (Reference Compound No. 11-1, 77 mg, 0.20 mmol), 3,4-diaminothiophene dihydrochloride (45 mg, 0.24 mmol), N,N-diisopropylethylamine (77 μL, 0.44 mmol) and HATU (90 mg, 0.24 mmol) in DMF (2.0 mL) was stirred at room temperature overnight. Water (30 mL) was added to the reaction solution, and then the whole was extracted with ethyl acetate (30 mL) three times. The organic layer was washed with water (30 mL) and brine (30 mL), dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel (NH-modified silica gel) column chromatography (chloroform-methanol) to give 55 mg of the title compound as a brown amorphous product. (Yield 58%)

後処理

  1. extractionthe whole was extracted with ethyl acetate (30 mL) three times
  2. washThe organic layer was washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel (NH-modified silica gel) column chromatography (chloroform-methanol)

出典と根拠

ORDレコード
ord-d281162df8b2459b9141a742f2525742
出典データセット
uspto-grants-2012_06
特許番号
US08198271B2

反応ノート

読み込み中…