Triethylamine → HCID 178425160, compound

HRID 1501097Notes

Reaction equation

HRID 1501097 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[CH:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)[CH3:9].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>[OH:60][C:53]1[C:52]([CH2:51][NH:50][C:14](=[O:16])[C:13]2[CH:12]=[CH:11][C:10]([CH:8]([N:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]3=[O:1])[CH3:9])=[CH:18][CH:17]=2)=[C:57]([CH3:58])[CH:56]=[C:55]([CH3:59])[N:54]=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 89585090HCID 89585090, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425160HCID 178425160, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-(2-oxopyridin-1(2H)-yl)ethyl)benzoic acid (111 mg, 0.46 mmol) in dichloromethane (20 mL) were added o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (285 mg, 0.75 mmol) and triethylamine (151 mg, 1.5 mmol). Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (76 mg, 0.5 mmol) was added. The mixture was stirred at room temperature for 12 hours. The resultant mixture was washed with water (20 mL×3) and the organic layer was concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-(2-oxopyridin-1(2H)-yl)ethyl)benzamide (57 mg, 33%). LRMS (M+H+) m/z: calcd 377.17. found 377. HPLC purity (214 nm): 98%. 1H NMR (300 MHz, d6-DMSO): δ 11.46 (s, 1H), 8.35-8.33 (m, 1H), 7.80 (d, J=8.1 Hz, 2H), 7.60-7.57 (m, 1H), 7.33-7.30 (m, 3H), 6.39 (d, J=9.3 Hz, 1H), 6.22-6.18 (m, 2H), 5.84 (s, 1H), 4.27 (s, 2H), 2.15 (s, 3H), 2.10 (s, 3H), 1.68 (d, J=7.2 Hz, 3H).

Workup

  1. washThe resultant mixture was washed with water (20 mL×3)
  2. concentrationthe organic layer was concentrated
  3. customto give a residue
  4. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-66433d8a87354698971c4969300f7a42
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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