Triethylamine → HCID 178425218, compound

HRID 2206505Notes

Reaction equation

HRID 2206505 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](O)=[O:18])=[C:9]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.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.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([NH:50][CH2:51][C:52]2[C:53]([OH:60])=[N:54][C:55]([CH3:59])=[CH:56][C:57]=2[CH3:58])=[O:18])=[C:9]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667434811-Benzyl-2-methyl-1H-indole-3-carboxylic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425218HCID 178425218, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-2-methyl-1H-indole-3-carboxylic acid (212 mg, 0.8 mmol) in dichloromethane (20 mL) was added 1H-benzo[d][1,2,3]triazol-1-ol (135 mg, 1 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (190 mg, 1 mmol) and triethylamine (252 mg, 2.5 mmol), and stirred at room temperature for 0.5 hour, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (152 mg, 1 mmol) was added and stirred for 4 hours. To the reaction mixture was added water (20 mL), which was extracted with dichloromethane (2×20 mL), combined and the organic layers were concentrated, the residue was purified by column chromatography (dichloromethane/methanol=20:1) to afford 1-benzyl-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-2-methyl-1H-indole-3-carboxamide (200 mg, 63%). LRMS (M+H+) m/z: calcd 399.19. found 399. HPLC purity (214 nm): 100%. 1H NMR (300 MHz, d6-DMSO): δ 11.61 (s, 1H), 7.80-7.69 (m, 2H), 7.46-7.42 (m, 1H), 7.30-7.22 (m, 3H), 7.11-7.07 (m, 2H), 6.98 (d, J=7.5 Hz, 2H), 5.89 (s, 1H), 5.46 (s, 2H), 4.33 (d, J=4.5 Hz, 2H), 2.57 (s, 3H), 2.26 (s, 3H), 2.11 (s, 3H).

Workup

  1. stirringstirred for 4 hours
  2. extractionwas extracted with dichloromethane (2×20 mL)
  3. concentrationthe organic layers were concentrated
  4. customthe residue was purified by column chromatography (dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-5b506c76329a45ffa464249ae43cce95
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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