1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Amino-4-[4-(2-methoxyethoxy)phenyl]-6-({[2-(4-morpholinyl)-1,3-thiazol-4-yl]-methyl}sulphanyl)pyridine-3,5-dicarbonitrile

HRID 2214980Notes

Reaction equation

HRID 2214980 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:12][CH:11]=2)[C:5]([C:21]#[N:22])=[C:4]([SH:23])[N:3]=1.Cl[CH2:25][C:26]1[N:27]=[C:28]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[S:29][CH:30]=1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:14][CH:15]=2)[C:5]([C:21]#[N:22])=[C:4]([S:23][CH2:25][C:26]2[N:27]=[C:28]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[S:29][CH:30]=2)[N:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15290886HCID 15290886, compoundHCID 178496105HCID 178496105, compound

Product 1

HCID 219490772-Amino-4-[4-(2-methoxyethoxy)phenyl]-6-({[2-(4-morpholinyl)-1,3-thiazol-4-yl]-methyl}sulphanyl)pyridine-3,5-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g (6.13 mmol) of 2-amino-4-[4-(2-methoxyethoxy)phenyl]-6-sulphanylpyridine-3,5-dicarbonitrile and 2.68 g (12.26 mmol) of 4-(4-(chloromethyl)-1,3-thiazol-2-yl]morpholine are dissolved in dry DMF (50 ml), and 1.83 ml (12.26 mmol) of DBU are added. After 3 hours of stirring at RT, the solvent is removed using a rotary evaporator and the residue is purified by preparative HPLC (column: Kromasil 100 C18 250×20 mm, 10 μm; acetonitrile/water gradient: 3 minutes of 10% acetonitrile which is then, over a period of 30 minutes, increased to 80% acetonitrile; flow rate: 25 ml/min). This gives 1.70 g (55% of theory) of product.

Workup

  1. customthe solvent is removed
  2. customa rotary evaporator
  3. customthe residue is purified by preparative HPLC (column
  4. custom3 minutes of 10% acetonitrile which
  5. waitover a period of 30 minutes
  6. temperatureincreased to 80% acetonitrile

Sources & evidence

ORD record
ord-0330e59f24904136ab879f6c6fa678e4
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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