Methyl[2-(pyridin-4-yl)ethyl]amine → HCID 22277839, compound

HRID 1064005Notes

Reaction equation

HRID 1064005 reaction equation
O=[S:2]1(=[O:29])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH:15][C:16]([O:18]CC3C=CC([N+]([O-])=O)=CC=3)=O)[CH:13]=[CH:14][C:3]1=2.O=S1C2C=CC=CC=2C2C=C(NC(OCC3C=CC([N+]([O-])=O)=CC=3)=O)C=CC1=2.[CH3:58][NH:59][CH2:60][CH2:61][C:62]1[CH:67]=[CH:66][N:65]=[CH:64][CH:63]=1>CCOC(C)=O>[O:29]=[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]2[CH:11]=[C:12]([NH:15][C:16]([N:59]([CH2:60][CH2:61][C:62]3[CH:67]=[CH:66][N:65]=[CH:64][CH:63]=3)[CH3:58])=[O:18])[CH:13]=[CH:14][C:3]1=2

Participants

5

Reactant 3

HCID 143276Methyl[2-(pyridin-4-yl)ethyl]amineHCID 22277824HCID 22277824, compoundHCID 69314014HCID 69314014, compound

Product 1

HCID 22277839HCID 22277839, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

5,5-Dioxo-2-(4-nitrobenzoxycarbonylamino)dibenzothiophene contaminated with 5-oxo-2-(4-nitrobenzoxycarbonylamino)dibenzothiophene (Examples 24 and 25; 396 mg, 1.0 mmol) was suspended in EtOAc (10 ml) and 4-[2-(methylamino)ethyl]pyridine (272 mg, 2.0 mmol) was added in one portion. The resulting mixture was stirred at ambient temperature for 16 hours then further EtOAc (100 ml) was added and the solution was washed with 1 M sodium hydroxide (2×25 ml), water (2×25 ml) and brine (25 ml), dried and evaporated in vacuo. The resulting mixture was separated by preparative HPLC (Dynamax C-18 60A column eluted with 20-90% acetonitrile in water plus 0.1% trifluoroacetic acid). Two products were obtained:

Workup

  1. washthe solution was washed with 1 M sodium hydroxide (2×25 ml), water (2×25 ml) and brine (25 ml)
  2. customdried
  3. customevaporated in vacuo
  4. customThe resulting mixture was separated by preparative HPLC (Dynamax C-18 60A column eluted with 20-90% acetonitrile in water plus 0.1% trifluoroacetic acid)
  5. customTwo products were obtained

Sources & evidence

ORD record
ord-8f5867d9f78b457894386117d908558d
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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