Triethylamine → HCID 178425147, compound

HRID 1501179Notes

Reaction equation

HRID 1501179 reaction equation
[CH:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[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.[NH2:46][CH2:47][C:48]1[C:49]([OH:56])=[N:50][C:51]([CH3:55])=[CH:52][C:53]=1[CH3:54]>ClCCl>[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:10]([NH:46][CH2:47][C:48]3[C:49]([OH:56])=[N:50][C:51]([CH3:55])=[CH:52][C:53]=3[CH3:54])=[O:12])=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5]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 141636714-Cyclopentylbenzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425147HCID 178425147, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyclopentylbenzoic acid (95 mg, 0.5 mmol) in dichloromethane (20 mL) were added o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (380 mg, 1 mmol) and triethylamine (202 mg, 2 mmol). The mixture was stirred for 0.5 hour. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (120 mg, 0.8 mmol) was added. After stirring at room temperature for 4 hours, the mixture was washed with water (50 mL). Organic phase was separated and concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) and to afford 4-cyclopentyl-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (35 mg, 22%) as white solid. LRMS (M+H+) m/z: calcd 324.18. found 324. HPLC purity (214 nm): 100%. 1H NMR (300 MHz, CD3OD): δ 7.71 (d, J=8.1 Hz, 2H), 7.32 (d, J=8.1 Hz, 2H), 6.10 (s, 1H), 4.48 (s, 2H), 3.08-3.02 (m, 1H), 2.36 (s, 3H), 2.24 (s, 3H), 2.10-2.05 (m, 2H), 1.84-1.62 (m, 6H).

Workup

  1. stirringAfter stirring at room temperature for 4 hours
  2. washthe mixture was washed with water (50 mL)
  3. customOrganic phase was separated
  4. concentrationconcentrated
  5. customto give a residue
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-8fca2ed5724c4cffbeeb018bc3020326
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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