Methyl[2-(pyridin-4-yl)ethyl]amine → 2-(N'-Pyrid-4-ylethyl-N'-methylureido)dibenzothiophene

HRID 2055308Notes

Reaction equation

HRID 2055308 reaction equation
[N+](C1C=CC(CO[C:10]([NH:12][C:13]2[CH:25]=[CH:24][C:16]3[S:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:15]=3[CH:14]=2)=[O:11])=CC=1)([O-])=O.[CH3:28][NH:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1>CCOC(C)=O>[N:35]1[CH:36]=[CH:37][C:32]([CH2:31][CH2:30][N:29]([CH3:28])[C:10](=[O:11])[NH:12][C:13]2[CH:25]=[CH:24][C:16]3[S:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:15]=3[CH:14]=2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 143276Methyl[2-(pyridin-4-yl)ethyl]amineHCID 693158012-(4-Nitrobenzoxycarbonylamino)dibenzothiophene

Product 1

HCID 98852872-(N'-Pyrid-4-ylethyl-N'-methylureido)dibenzothiophene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2-(4-Nitrobenzoxycarbonylamino)dibenzothiophene (Example 1; 501 mg, 1.35 mmol) was suspended in EtOAc (10 ml) and 4-[2-(methylamino)ethyl]pyridine (408 mg, 3.0 mol) added in one portion. The resulting mixture was stirred at ambient temperature for 16 hours then further EtOAc (50 ml) added. The solution was washed with 1 M sodium hydroxide (3×25 ml), water (2×25 ml) and brine (25 ml), dried and evaporated in vacuo. NMR 8.44 (m, 3H), 8.34 (d, 1H), 8.13 (m, 1H), 7.96 (m, 1H), 7.82 (d, 1H), 7.55 (dd, 1H), 7.47 (m, 2H), 7.28 (d, 2H), 3.61 (t, 2H), 2.96 (s, 3H), 2.86 (t, 2H); m/z 362.

Workup

  1. washThe solution was washed with 1 M sodium hydroxide (3×25 ml), water (2×25 ml) and brine (25 ml)
  2. customdried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-1ee63dc9aa99485c88110b08c5b9c7ae
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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