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

HRID 2055313Notes

Reaction equation

HRID 2055313 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-517816486ed44fb18cf9ed39458ed0b2
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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