1,2-Dichloroethane → (E)-N-methyl-N-(2-methyl-1H-indol-3-yl methyl)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamide

HRID 1690406Notes

Reaction equation

HRID 1690406 reaction equation
[CH2:1](Cl)[CH2:2]Cl.Cl.[O:6]=[C:7]1[NH:13][C:12]2[N:14]=[CH:15][C:16](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:17][C:11]=2[CH2:10][CH2:9][CH2:8]1.[CH3:23][C:24]1[NH:25][C:26]2[C:31]([C:32]=1[CH2:33][NH:34][CH3:35])=[CH:30][CH:29]=[CH:28][CH:27]=2.[CH:36]1C=CC2N(O)N=NC=2C=1.[OH2:46].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:36][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:31][CH2:32][CH2:24][CH2:23][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:17]=[CH:16]/[CH2:18][CH:19]1[C:20](=[O:21])[O:22][C:2](=[O:46])[CH2:1]1.[CH3:35][N:34]([CH2:33][C:32]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][C:24]=1[CH3:23])[C:20](=[O:22])/[CH:19]=[CH:18]/[C:16]1[CH:15]=[N:14][C:12]2[NH:13][C:7](=[O:6])[CH2:8][CH2:9][CH2:10][C:11]=2[CH:17]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10954023N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amineHCID 66905085(E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylic acid hydrochloride

Product 2

HCID 53631032,5-Furandione, dihydro-3-(2-octadecen-1-yl)-HCID 10023175(E)-N-methyl-N-(2-methyl-1H-indol-3-yl methyl)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylamideYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (0.18 g, 0.96 mmole) was added to a solution of (E)-3-(8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl)acrylic acid hydrochloride salt (0.24 g, 0.87 mmole), 2-methyl-3-(methylaminomethyl)indole (0.15 g, 0.87 mmole), HOBt.H2O (0.13 g., 0.96 mmole) and diisopropylethylamine (0.45 mL, 2.61 mmole) in DMF (15 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over Na2SO4. Preparative HPLC on a Waters C-18 ODSA column (gradient: 20-100% H2O/CH3CN) gave the title compound (0.13 g, 38%) as a light yellow solid after drying in vacuo: MS (ES) m/e 389 (M+H)+.

Workup

  1. customat RT
  2. concentrationthen was concentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-ceccd9a4a49e436c9e0e9818a27657ae
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

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