Triethylamine → 2-[(1S)-1-({[[2-(Dimethylammonio)ethyl](methyl)amino]-sulfonyl}amino)-7-oxooctyl]-5-phenyl-1H-imidazol-1-ium bis(trifluoroacetate)

HRID 251726Notes

Reaction equation

HRID 251726 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([O-:12])=[O:11].[NH3+:15][C@H:16]([C:25]1[NH2+:26][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:28][N:29]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23].CCN(CC)CC.[Cl-].Cl[S:45]([N:48]([CH3:54])[CH2:49][CH2:50][NH+:51]([CH3:53])[CH3:52])(=[O:47])=[O:46]>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([O-:12])=[O:11].[CH3:52][NH+:51]([CH3:53])[CH2:50][CH2:49][N:48]([CH3:54])[S:45]([NH:15][C@H:16]([C:25]1[NH2+:26][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:28][N:29]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23])(=[O:47])=[O:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 866279482-[(1S)-1-Ammonio-7-oxooctyl]-5-phenyl-1H-imidazol-1-ium bis(trifluoroacetate)HCID 866279522-[(Chlorosulfonyl)(methyl)amino]-N,N-dimethylethanaminium chloride

Product 1

HCID 866279532-[(1S)-1-({[[2-(Dimethylammonio)ethyl](methyl)amino]-sulfonyl}amino)-7-oxooctyl]-5-phenyl-1H-imidazol-1-ium bis(trifluoroacetate)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution Example 1, A3 and Et3N (4 eq.) in DCM was added crude C1 (1.2 eq). The mixture was stirred at RT for 16 hr. The mixture 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 C2 as a colourless oil. 1H NMR (300 MHz, DMSO-d6) δ: 8.18 (1H, br. s), 7.87 (1H, br. s), 7.83-7.71 (2H, m), 7.58-7.28 (3H, m), 4.64-4.45 (1H, m), 3.41-3.16 (4H, m), 2.79 (6H, s), 2.63 (3H, s), 2.39 (2H, t, J=6.8 Hz), 2.05 (3H, s), 1.98-1.78 (2H, m), 1.53-1.19 (6H, m). MS (ES) C22H35N5O3S requires: 449, found: 450 (M+H)+.

Workup

  1. customThe mixture was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-4780e484ac5044949b87094c31d3cd72
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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