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

HRID 1064000Notes

Reaction equation

HRID 1064000 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 mmol) 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-a2c79396a6da430a820c46c5c44104ee
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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