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

HRID 217642

반응식

HRID 217642 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-d281162df8b2459b9141a742f2525742
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198271B2

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