3-Aminopyridine → HCID 66635259, compound

HRID 2204760Notes

Reaction equation

HRID 2204760 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[C:16]([C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[C:15]([C:26]([F:29])([F:28])[F:27])=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=[N:54][C:49]2[CH:50]=[CH:51][CH:52]=[N:53][C:48]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NC1C=NC=CC=1>CN(C)C=O>[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[C:16]([C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[C:15]([C:26]([F:29])([F:27])[F:28])=[CH:14][C:10]=2[C:11]([NH:54][C:49]2[CH:48]=[N:53][CH:52]=[CH:51][CH:50]=2)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

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 66611936HCID 66611936, compound

Product 1

HCID 66635259HCID 66635259, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[(Phenylmethyl)oxy]-4-(1-piperidinylcarbonyl)-5-(trifluoromethyl)benzoic acid (may be prepared as described in Description 58; 69 mg) was dissolved in N,N-dimethylformamide (4 ml). Diisopropylethylamine (0.06 ml, 0.34 mmol) and HATU (130 mg, 0.34 mmol) were added, the solution was stirred for 5 minutes then 3-aminopyridine (32.2 mg, 0.34 mmol) was added. The solution was stirred for 90 minutes, the solvent was removed in vacuo and the residue purified by MDAP to give the title compound as a white solid. 29 mg.

Workup

  1. stirringThe solution was stirred for 90 minutes
  2. customthe solvent was removed in vacuo
  3. customthe residue purified by MDAP

Sources & evidence

ORD record
ord-3ecfc84b576941e58dc5e5f389c4dd7a
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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