Pyridine → HCID 67661393, compound

HRID 724914Notes

Reaction equation

HRID 724914 reaction equation
C[C:2]([O:5]C(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)(C)C.[CH2:18]([N:26]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=2)[C:27]1=[O:41])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].N1C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[NH3:7].[CH3:2][OH:5].[NH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][S:37]([C:34]2[CH:35]=[CH:36][C:31]([N:28]3[CH2:29][CH2:30][N:26]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:27]3=[O:41])=[CH:32][CH:33]=2)(=[O:39])=[O:38])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 382207Tert-butyl 4-aminophenethylcarbamateHCID 19711294HCID 19711294, compound

Product 2

HCID 21705897Ammonia methanolYield 10%HCID 67661393HCID 67661393, compoundYield 173%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 118 mg (0.499 mmol) of 2-(4-aminophenyl)ethylcarbamic acid 1,1-dimethylethyl ester (for synthesis see M. H. Fisher, E. R. Parmee, M. R. Mathvink, A. E. Weber, European Patent Application 0 611 003 A1) in 5 mL of dichloromethane was treated with 195.7 mg (0.525 mmol) of 4-(3-octyl-2-imidazolidinon-1-yl)benzenesulfonyl chloride from Example 6 and 40 μL (0.495 mmol) of pyridine. After stirring for 16 h, 1.5 mL of trifluoroacetic acid was added and the reaction mixture stirred for 0.75 h. The volatile components were removed in vacuo. Flash chromatography (silica gel, 5-10% (10% ammonia-methanol)-methylene chloride) afforded 204 mg (86%) of the title compound as a white powder: 1H NMR (400 MHz, CDCl3) δ7.65 (d, 2H, J=9.2 Hz), 7.58 (d, 2H, J=9.2 Hz), 7.03 (d, 2H, J=8.6 Hz), 6.96 (d, 2H, J=8.5 Hz), 3.80-3.76 (m, 2H), 3.50-3.46 (m, 2H), 3.26 (t, 2H, J=7.4 Hz), 2.88 (t, 2H, 6.8 Hz), 2.65 (t, 2H, J=6.9 Hz) 1.65-1.60 (m, 2H), 1.29-1.23 (m, 10H), 0.85 (m, 3H).

Workup

  1. stirringthe reaction mixture stirred for 0.75 h
  2. customThe volatile components were removed in vacuo

Sources & evidence

ORD record
ord-e9825c3b9c9b4b7b81faed87b55b69e7
Source dataset
uspto-grants-1998_01
Patent number
US05705515

Reaction notes

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