Triethylamine → HCID 178425223, compound

HRID 1527028Notes

Reaction equation

HRID 1527028 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([OH:21])=O)=[C:11]2[CH3:22])[CH3:9])=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(CC)CC.[NH2:51][CH2:52][C:53]1[C:54]([OH:61])=[N:55][C:56]([CH3:60])=[CH:57][C:58]=1[CH3:59]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([NH:51][CH2:52][C:53]3[C:54]([OH:61])=[N:55][C:56]([CH3:60])=[CH:57][C:58]=3[CH3:59])=[O:21])=[C:11]2[CH3:22])[CH3:9])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 117778747HCID 117778747, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425223HCID 178425223, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1-(4-chlorophenyl)ethyl)-2-methyl-1H-indole-3-carboxylic acid (200 mg, 0.64 mmol) in anhydrous DCM (5 mL) was added HOBt (130 mg, 0.96 mmol), EDCI (184 mg, 0.96 mmol) and Et3N (194 mg, 1.92 mmol) at room temperature under N2. The reaction was stirred for 30 min and then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (107 mg, 0.7 mmol) was added. The reaction was stirred at room temperature overnight. The mixture was diluted with water and adjusted to pH 7 and extracted with DCM. The crude product was purified by silica gel chromatography (Eluent: DCM:MeOH=30:1) to afford the title compound a yellow solid. (120 mg, yield 41.9%) 1H NMR (DMSO-d6, 400 MHz) δ 11.6 (s, 1H), 7.74-7.68 (m, 2H), 7.39 (dd, J1=2.0 Hz, J2=6.8 Hz, 2H), 7.16 (d, J=8.4 Hz, 2H), 7.06-6.93 (m, 3H), 5.92 (t, J=7.2 Hz, 2H), 4.33 (d, J=5.6 Hz, 2H), 2.59 (s, 3H), 2.26 (s, 3H), 2.11 (s, 3H), 1.87 (d, J=7.2 Hz, 3H); ESI-MS: m/z 447.8 [M+H]+.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionextracted with DCM
  3. customThe crude product was purified by silica gel chromatography (Eluent: DCM:MeOH=30:1)

Sources & evidence

ORD record
ord-5a2fe6beccdf461bb1486c3aeee9cff8
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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