1-Hydroxybenzotriazole → HCID 89581305, compound

HRID 1501195Notes

Reaction equation

HRID 1501195 reaction equation
[O:1]([CH2:8][CH:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][CH2:21][C:22]1[C:23](O)=[N:24][C:25]([CH3:29])=[CH:26][C:27]=1[CH3:28].ON1C2C=CC=C[C:35]=2N=N1.Cl.CN(C)CCCN=C=NCC>ClCCl.C(OCC)(=O)C.C(N(CC)CC)C>[O:1]([CH2:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([NH:20][CH2:21][C:22]2[C:23]([CH3:35])=[N:24][C:25]([CH3:29])=[CH:26][C:27]=2[CH3:28])=[O:17])=[CH:18][CH:19]=1)[CH3:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89581499HCID 89581499, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 89581305HCID 89581305, compoundYield 77.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture solution of 4-(1-phenoxypropan-2-yl)benzoic acid (60 mg, 0.2 mmol), 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (37 mg, 0.2 mmol), 1-Hydroxybenzotriazole (30 mg, 0.2 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (40 mg, 0.2 mmol) and triethylamine (0.1 mL) in dichloromethane (50 mL) was stirred at room temperature for 18 hours. The mixture solution was diluting with ethyl acetate (50 mL), washed with water (20 mL). The organic layer was concentrated to dry. The residue was purified by column chromatography (silica-gel, dichloromethane/methanol=30:1) to give 4-(1-phenoxypropan-2-yl)-N-((2,4,6-trimethylpyridin-3-yl)methyl)benzamide as a yellow solid (60 mg, 64%). LRMS (M+H+) m/z: calcd 391.19. found 391. HPLC Purity (214 nm): 95%. 1H NMR (300 MHz, CDCl3): δ 7.70-7.78 (m, 3H), 7.21-7.31 (m, 4H), 6.82-6.94 (m, 3H), 5.91 (s, 1H), 4.54-4.56 (m, 2H), 3.93-4.07 (m, 2H), 3.24-3.28 (m, 1H), 2.38 (s, 3H), 2.25 (s, 3H), 1.39 (d, J=6 Hz, 3H).

Workup

  1. washwashed with water (20 mL)
  2. concentrationThe organic layer was concentrated
  3. customto dry
  4. customThe residue was purified by column chromatography (silica-gel, dichloromethane/methanol=30:1)

Sources & evidence

ORD record
ord-f68dc1f07fae48d3b75f8f62cb03feb3
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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