3-Aminopyridine → HCID 51357237, compound

HRID 1623768Notes

Reaction equation

HRID 1623768 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])=[C:6]([CH:11]=1)[C:7]([O:9]C)=O.C[Si](C)(C)[O-].[K+].CCN(C(C)C)C(C)C.[NH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])=[C:6]([CH:11]=1)[C:7]([NH:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)=[O:9]

Participants

7

Reactant 5

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23668039Potassium trimethylsilanolateHCID 67106856HCID 67106856, compound

Product 1

HCID 51357237HCID 51357237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-bromo-2-{[(1S)-1-phenylethyl]oxy}benzoate (may be prepared as described in Description 99; 100 mg, 0.30 mmol) in THF (2 ml) was added potassium trimethylsilanolate (115 mg, 0.90 mmol). The mixture was stirred for 45 minutes. The solvent was removed and the residue redissolved in DMF (2 ml). To the solution was added DIPEA (0.13 ml, 0.75 mmol), 3-aminopyridine (56 mg, 0.60 mmol) and HATU (170 mg, 0.45 mmol). The solution was stirred for 18 hours. The solvent was removed in vacuo and purified by MDAP to give the titled example as a colourless gum. 73 mg.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue redissolved in DMF (2 ml)
  3. stirringThe solution was stirred for 18 hours
  4. customThe solvent was removed in vacuo
  5. custompurified by MDAP
  6. customto give the titled example as a colourless gum

Sources & evidence

ORD record
ord-f1bf3662e56946228b5153f0c22c3360
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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