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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 18334
Notes
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Reaction equation

HRID 18334 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 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 5363103
2,5-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 76.9%

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

Sources & evidence

ORD record
ord-3a6af946cc7a4546a338c94184e70f94
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741339B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes