Triethylamine → HCID 136041457, compound

HRID 602116Notes

Reaction equation

HRID 602116 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]1.[OH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][N:22]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[OH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:13][CH:10]2[CH2:9][CH2:8][N:7]([C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:12][CH2:11]2)=[O:26])=[CH:23][N:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 47782331-(Pyrimidin-2-yl)piperidin-4-amineHCID 1357414751033845-00-9

Product 1

HCID 136041457HCID 136041457, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

1-pyrimidin-2-ylpiperidin-4-amine (45 mg, 0.25 mmol) was added to a solution of 6-(2-hydroxyphenyl)nicotinic acid (50 mg, 0.23 mmol) in DMF (0.25 ml) and triethylamine (0.176 ml, 1.26 mmol). O-(1H-Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (125 mgs, 0.33 mmol) in DMF (0.5 ml) was then added and the reaction sealed. The reaction was shaken at 50° C. for 16 hours. The reaction was then evaporated to dryness in vacuo. Dichloromethane (2 ml) and saturated aqueous sodium hydrogen carbonate (0.5 ml) were added, the sealed reaction was shaken vigorously for 2 h. After this time the plates were opened and the biphasic mixture filtered through an Isolute SPE phase separation tube. The organic layer (filtrate) was evaporated to dryness in vacuo. DMSO (1 ml) was then added and the plate sealed and shaken at 50° C. until all the residue had dissolved then purified by reverse phase preparative HPLC using method B as defined below. R.T. 3.06 MS ES m/z 376 [M+H]+. This gave the title compound.

Workup

  1. customthe reaction sealed
  2. customThe reaction was then evaporated to dryness in vacuo
  3. additionDichloromethane (2 ml) and saturated aqueous sodium hydrogen carbonate (0.5 ml) were added
  4. customthe sealed reaction
  5. stirringwas shaken vigorously for 2 h
  6. filtrationthe biphasic mixture filtered through an Isolute SPE phase separation tube
  7. customThe organic layer (filtrate) was evaporated to dryness in vacuo
  8. additionDMSO (1 ml) was then added
  9. customthe plate sealed
  10. stirringshaken at 50° C. until all the residue
  11. dissolutionhad dissolved
  12. customthen purified by reverse phase preparative HPLC
  13. customR.T

Sources & evidence

ORD record
ord-a32c85ce6dae4da5b8ee13b3be84c097
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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