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

Reaction equation

HRID 251727 reaction equation
[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]

Participants

8

Reactant 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)

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d3eee426e5a44a53908a0e37df5d4eef
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Linked notes

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