Triethylamine → HCID 178425233, compound

HRID 2206477Notes

Reaction equation

HRID 2206477 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16](O)=[O:17])=[CH:8]1.[NH2:20][CH2:21][C:22]1[C:23]([OH:30])=[N:24][C:25]([CH3:29])=[CH:26][C:27]=1[CH3:28].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[OH:30][C:23]1[C:22]([CH2:21][NH:20][C:16]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:19])[CH:8]=2)=[O:17])=[C:27]([CH3:28])[CH:26]=[C:25]([CH3:29])[N:24]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89739830HCID 89739830, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425233HCID 178425233, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(o-tolyl)-1H-indole-3-carboxylic acid (100 mg, 0.398 mmol), 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (60 mg, 0.398 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (114 mg, 0.597 mmol). N-hydroxybenzotriazole (81 mg, 0.597 mmol), triethylamine (81 mg, 0.796 mmol) and dichloromethane (5 mL) was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure and ethyl acetate (10 mL) was added. The resulting mixture was washed with water (10 mL) and brine in turns and then dried over sodium sulfate. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by preparative-TLC (silica gel, dichloromethane:methanol=15:1) to give pure desired product of N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-1-(o-tolyl)-1H-indole-3-carboxamide as an off white solid (100 mg, 65%). LRMS (M+H+) m/z: calcd 385.18. found 385. 1H NMR (300 MHz, CD3OD) δ 8.16 (dd, J=6.1, 2.5 Hz, 1H), 7.87 (s, 1H), 7.44 (d, J=4.9 Hz, 2H), 7.41-7.26 (m, 2H), 7.26-7.12 (m, 2H), 6.93 (dd, J=6.3, 2.4 Hz, 1H), 6.11 (s, 1H), 4.53 (s, 2H), 2.41 (s, 3H), 2.24 (s, 3H), 2.01 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure and ethyl acetate (10 mL)
  2. additionwas added
  3. washThe resulting mixture was washed with water (10 mL) and brine in turns
  4. dry with materialdried over sodium sulfate
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by preparative-TLC (silica gel, dichloromethane:methanol=15:1)

Sources & evidence

ORD record
ord-e4dfa6c93a4b42709648316d776d4e78
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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