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Dimethylformamide → N-[5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yl)pentyl]-3-(imidazol-4-yl)propionamide bis maleate hemihydrate

HRID 2413199
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HRID 2413199 반응식
ClC([O:4][CH2:5][CH3:6])=[O:3].[NH:7]1[CH:11]=[C:10]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[N:9]=[CH:8]1.C(N(CC)CC)C.[F:24][C:25]([F:44])([F:43])[CH2:26][N:27]=[C:28]([NH2:42])[NH:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])[N:31]=1.CN([CH:48]=[O:49])C>>[OH2:3].[C:5]([OH:4])(=[O:49])/[CH:6]=[CH:13]\[C:14]([OH:16])=[O:15].[C:48]([OH:49])(=[O:3])/[CH:12]=[CH:13]\[C:14]([OH:16])=[O:15].[F:44][C:25]([F:24])([F:43])[CH2:26][N:27]=[C:28]([NH2:42])[NH:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:14](=[O:16])[CH2:13][CH2:12][C:10]2[N:9]=[CH:8][NH:7][CH:11]=2)[N:31]=1.[F:44][C:25]([F:24])([F:43])[CH2:26][N:27]=[C:28]([NH2:42])[NH:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:14](=[O:16])[CH2:13][CH2:12][C:10]2[N:9]=[CH:8][NH:7][CH:11]=2)[N:31]=1.[C:5]([OH:4])(=[O:49])/[CH:6]=[CH:13]\[C:14]([OH:16])=[O:15].[C:5]([OH:4])(=[O:49])/[CH:6]=[CH:13]\[C:14]([OH:16])=[O:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 6228Dimethylformamide2회HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 202086774-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(5-aminopentyl)pyrimidineHCID 178525356HCID 178525356, 화합물

생성물 1

HCID 178512205
N-[5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yl)pentyl]-3-(imidazol-4-yl)propionamide bis maleate hemihydrate

실험 절차

Ethyl chloroformate (0.14 ml.) was added to a stirred mixture of 3-(imidazol-4-yl)propionic acid (0.3 g.) and triethylamine (2 ml.) in DMF (5 ml.) at 0° and the mixture stirred at 0° for 0.5 hours. 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(5-aminopentyl)pyrimidine (0.3 g.) in DMF (2 ml.) was added to the mixture and stirring was continued at room temperature for 16 hours. The mixture was evaporated and the residue partitioned between EtOAc and 2 N aqueous HCl. The acid layer was basified with 11 N aqueous NaOH, extracted with EtOAc, dried (MgSO4) and evaporated to dryness. The residual gum was dissolved in EtOAc and treated with excess of a solution of maleic acid in EtOAc. The resulting solid was filtered and recrystallised from EtOH/EtOAc to give N-[5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yl)pentyl]-3-(imidazol-4-yl)propionamide bis maleate hemihydrate (containing 0.5 EtOH of crystallisation) (0.2 g.), m.p. 136°-141° (decomp.).

후처리

  1. stirringstirring
  2. waitwas continued at room temperature for 16 hours
  3. customThe mixture was evaporated
  4. customthe residue partitioned between EtOAc and 2 N aqueous HCl
  5. extractionextracted with EtOAc
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. dissolutionThe residual gum was dissolved in EtOAc
  9. additiontreated with excess of a solution of maleic acid in EtOAc
  10. filtrationThe resulting solid was filtered
  11. customrecrystallised from EtOH/EtOAc

출처 및 근거

ORD 기록
ord-bd2c05f0aa0c4aa8b5265f01aa05792e
출처 데이터셋
uspto-grants-1985_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04496571

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