Trifluoroacetic acid → HCID 66850877, compound

HRID 873653Notes

Reaction equation

HRID 873653 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[S:19](=[O:22])(=[O:21])[NH2:20].C(N=C=NCCCN(C)C)C.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C.[N:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[CH2:57][CH2:58][NH2:59].FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH:59][CH2:58][CH2:57][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][N:51]=3)=[O:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][C:3]=1[S:19](=[O:21])(=[O:22])[NH2:20]

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 759192-PyridineethanamineHCID 181649HOAtHCID 58107387HCID 58107387, compound

Product 1

HCID 66850877HCID 66850877, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Chloro-3-sulfamoyl-benzoyl)-benzoic acid (50 mg, 0.15 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (57 mg, 0.30 mmol), 1-hydroxy-7-azabenzotriazole (41 mg, 0.30 mmol) were dissolved in dichloromethane (5 mL), then triethylamine (61 mg, 0.60 mmol) is added followed by 2-pyridin-2-yl-ethylamine (23 mg, 0.19 mL) and the reaction is allowed to stir at ambient temperature overnight. The reaction is then quenched with trifluoroacetic acid (1 mmol) and loaded directly onto a silica gel column, chromatography (gradient of ethyl acetate in hexanes 10-100%) followed by crystallization from ether afforded 20 mg of the title compound. 1H NMR (DMSO) 3.02 (t, 2H, J=7.57 Hz), 3.63-3.68 (m, 2H), 7.22-7.25 (m, 1H), 7.30 (d, 1H, J=7.83 Hz), 7.70-7.74 (m, 1H), 7.83-7.87 (m, 5H), 7.92-7.99 (m, 3H), 8.31 (d, 1H, J=2.02), 8.51-8.53 (m, 1H), 8.85-8.82 (m, 1H). MS (m/z): 442 (M−1). CHN Calc C, 56.82; H, 4.09; N, 9.47. Found C, 55.65; H, 3.90; N, 9.22 (+0.5 water).

Workup

  1. customfollowed by crystallization from ether

Sources & evidence

ORD record
ord-a2a921e817f3425bb83ca5904ac4d6ad
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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