Triethylamine → HCID 178425165, compound

HRID 1501175Notes

Reaction equation

HRID 1501175 reaction equation
[CH:1]1([O:7][CH:8]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:50][CH2:51][C:52]1[C:53]([OH:60])=[N:54][C:55]([CH3:59])=[CH:56][C:57]=1[CH3:58]>ClCCl>[CH:1]1([O:7][CH:8]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([NH:50][CH2:51][C:52]3[C:53]([OH:60])=[N:54][C:55]([CH3:59])=[CH:56][C:57]=3[CH3:58])=[O:16])=[CH:17][CH:18]=2)[CH3:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89581348HCID 89581348, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425165HCID 178425165, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 4-(1-(cyclohexyloxy)ethyl)benzoic acid (62 mg, 0.25 mmol) in dichloromethane (80 mL) was added o-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (143 mg, 0.38 mmol) and triethylamine (76 mg, 0.75 mmol). then the 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (131 mg, 0.86 mmol) was added, the solution was stirred at room temperature for 12 hours, then washed with water (50 mL*3), the organic layer was evaporate ed and purified by column chromatography (silica gel, dichloromethane/meth anol=20:1) to give 4-(1-(cyclohexyloxy)ethyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (57 mg, 60%). LRMS (M+H+) m/z: calcd: 382.23. found 382; 1H-NMR (300 MHz, CD3OD) δ 7.76 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 6.11 (s, 1H), 4.69-4.67 (m, 1H), 4.49 (s, 2H), 3.20-3.14 (m, 1H), 2.37 (s, 3H), 2.24 (s, 3H), 1.69 (m. 1H), 1.51-1.49 (m, 3H), 1.38-1.36 (m, 1H), 1.29-1.20 (m, 8H).

Workup

  1. washwashed with water (50 mL*3)
  2. customthe organic layer was evaporate ed
  3. custompurified by column chromatography (silica gel, dichloromethane/meth anol=20:1)

Sources & evidence

ORD record
ord-cab69a3f1b4c45b5a23ba3196485103b
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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