Triethylamine → 2-((1S)-1-{[(5-Methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-7-oxooctyl)-5-phenyl-1H-imidazol-1-ium trifluoroacetate

HRID 251727

반응식

HRID 251727 반응식
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].F[C:9](F)(F)[C:10]([O-:12])=O.C[NH+]1CCCC(C([NH:24][C@H:25]([C:34]2[NH2+:35][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:37][N:38]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]C(=O)C)=O)C1.F[C:46](F)(F)[C:47]([O-:49])=O.F[C:53](F)(F)C([O-])=O.[NH3+][C@H:60]([C:69]1[NH2+:70][C:71]([C:74]2[CH:79]=CC=CC=2)=[CH:72]N=1)[CH2:61]CCCCC(=O)C.CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.COC1C=C2C(=CC=1)NC(C)=C2CC(O)=O>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH3:53][O:49][C:47]1[CH:46]=[C:79]2[C:69](=[CH:60][CH:61]=1)[NH:70][C:71]([CH3:72])=[C:74]2[CH2:9][C:10]([NH:24][C@H:25]([C:34]1[NH2+:35][C:36]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[CH:37][N:38]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:3](=[O:5])[CH3:2])=[O:12]

참가 물질

8

반응물 6

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 761515-Methoxy-2-methylindole-3-acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866279482-[(1S)-1-Ammonio-7-oxooctyl]-5-phenyl-1H-imidazol-1-ium bis(trifluoroacetate)HCID 873313811-methyl-3-({[(1S)-7-oxo-1-(5-phenyl-1h-imidazol-1-ium-2-yl)octyl]amino}carbonyl)piperidinium bis(trifluoroacetate)

생성물 1

HCID 866279552-((1S)-1-{[(5-Methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}-7-oxooctyl)-5-phenyl-1H-imidazol-1-ium trifluoroacetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a solution of Example 1, A3 and Et3N (1 eq.) in DCM was added a solution of EDC hydrochloride (1.2 eq.), HOBt (1.2 eq.) and (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (1.2 eq.) in DCM. The mixture was shaken at RT for 1.5 hr and then the reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified by preparative RP-HPLC, using H2O (0.1% TFA) and MeCN (+0.1% TFA) as eluents (column: C18). The desired fractions were lyophilized to afford the titled compound D1 as a white fluffy powder.

후처리

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by preparative RP-HPLC

출처 및 근거

ORD 기록
ord-d3eee426e5a44a53908a0e37df5d4eef
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863294B2

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