Triethylamine → HCID 178425217, compound

HRID 2206514Notes

Reaction equation

HRID 2206514 reaction equation
[CH3:1][C:2]1[N:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4]2[C:9]([C:10]=1[C:11](O)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.N1(O)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:37][CH2:38][C:39]1[C:40]([OH:47])=[N:41][C:42]([CH3:46])=[CH:43][C:44]=1[CH3:45]>ClCCl.O>[OH:47][C:40]1[C:39]([CH2:38][NH:37][C:11]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:2]=2[CH3:1])=[O:12])=[C:44]([CH3:45])[CH:43]=[C:42]([CH3:46])[N:41]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 89741115HCID 89741115, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425217HCID 178425217, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-1-phenyl-1H-indole-3-carboxylic acid (115 mg, 0.46 mmol) in anhydrous dichloromethane (3 mL) was added 1H-benzo[d][1,2,3]triazol-1-ol (75 mg, 0.55 mmol), 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (106 mg, 0.55 mmol) and triethylamine (0.16 mL, 1.15 mmol). The mixture was stirred at room temperature for half an hour, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (70 mg, 0.46 mmol) was added and stirred at room temperature for 3 hours. The reaction mixture was added water (20 mL), extracted with dichloromethane (20 mL×2), combined and concentrated the organic layers to give the residue, which was purified by column chromatography (silica gel, dichloromethane/methanol=25:1) to afford N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-1-phenyl-1H-indole-3-carboxamide (12 mg, 50% yield. LRMS (M+H+) m/z: calcd for 385.18. found 385. 1H NMR (300 MHz, CDCl3) δ 12.62 (s, 1H), 7.89 (d, J=8.0 Hz, 1H), 7.77-7.40 (m, 3H), 7.43-7.18 (m, 3H), 7.22-7.00 (m, 2H), 5.98 (s, 1H), 4.65 (s, 2H), 2.60-2.52 (m, 3H), 2.45 (s, 3H), 2.25 (s, 3H).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. extractionextracted with dichloromethane (20 mL×2)
  3. concentrationconcentrated the organic layers
  4. customto give the residue, which
  5. customwas purified by column chromatography (silica gel, dichloromethane/methanol=25:1)

Sources & evidence

ORD record
ord-724eb9ddc4c24f3fa5e1c1f6a9f55cb6
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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