4-Methylmorpholine → HCID 68426121, compound

HRID 1785608Notes

Reaction equation

HRID 1785608 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][N:13]1[CH2:17][CH:16]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[N:15]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:14]1=[O:37].CN1CCOCC1.Cl[S:46]([CH2:49][C:50]([O:52][CH2:53][CH:54]1[C:66]2[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=2[C:60]2[C:55]1=[CH:56][CH:57]=[CH:58][CH:59]=2)=[O:51])(=[O:48])=[O:47]>ClCCl>[CH:56]1[C:55]2[CH:54]([CH2:53][O:52][C:50](=[O:51])[CH2:49][S:46]([NH:12][N:13]3[CH2:17][CH:16]([C:18]4[CH:23]=[CH:22][C:21]([CH:24]5[CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[N:15]([CH2:27][CH2:28][C:29]4[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=4)[C:14]3=[O:37])(=[O:47])=[O:48])[C:66]3[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=3)[C:60]=2[CH:59]=[CH:58][CH:57]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 11142292HCID 11142292, compoundHCID 86617154HCID 86617154, compound

Product 1

HCID 68426121HCID 68426121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-amino-3-[2-(4-methoxyphenyl)ethyl]-4-(4-cyclopropylphenyl)-2-imidazolidinone p-toluenesulfonic acid salt (2.61 g, 0.0050 mol), dichloromethane (12 mL), and N-methylmorpholine (1.53 mL, 0.014 mol) is added a solution of 9H-fluoren-9-ylmethyl chlorosulfonylacetate, 14, (1.76 g, 0.0052 mol) in dichloromethane (7 mL) slowly over 7 minutes at 15° C. to 20° C. The reaction is stirred at ambient temperature for 45 minutes, and then washed twice with 0.1 N HCl and water. The organic phase is dried (sodium sulfate) and concentrated to a foamy solid. The residue is purified over silica (0%-50% ethyl acetate/hexanes gradient) to afford 2.1 g of the desired compound. 1H NMR (CDCl3) δ 7.81 (d, J=7.5 Hz, 2H), 7.69 (d, J=7.5 Hz, 2H), 7.45 (m, 2H), 7.36 (m, 2H), 7.27 (s, 1H), 7.17 (m, 2H), 7.10 (m, 2H), 7.02 (m, 2H), 6.82 (m, 2H), 4.63 (m, 2H), 4.45 (t, J=8.4 Hz, 1H), 4.35 (m, 3H), 3.94 (t, J=8.4 Hz, 1H), 3.78 (s, 3H), 3.65 (m, 1H), 3.38 (t, J=8.1 Hz, 1H), 2.92 (m, 1H), 2.74 (m, 1H), 2.64 (m, 1H), 1.94 (m, 1H), 1.03 (m, 2H), 0.74 (m, 2H). MS 652 (MH+). Anal. calcd. for C37H37N3O6S¾H2O: C, 66.80; H, 5.83; N, 6.32. Found: C, 66.78; H, 5.72; N, 6.30.

Workup

  1. washwashed twice with 0.1 N HCl and water
  2. dry with materialThe organic phase is dried (sodium sulfate)
  3. concentrationconcentrated to a foamy solid
  4. customThe residue is purified over silica (0%-50% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-77747453736c49cdb794f9713a81a45d
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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