1,2-Dichloroethane → HCID 131732560, compound

HRID 873400Notes

Reaction equation

HRID 873400 reaction equation
CC([N:4]1[C:12]2[C:11]([O:13][CH3:14])=[CH:10][CH:9]=[C:8]([C:15]([OH:17])=O)[C:7]=2[CH:6]=[CH:5]1)C.[NH2:18][CH2:19][C:20]1[C:21](=[O:30])[NH:22][C:23]([CH3:29])=[CH:24][C:25]=1[CH2:26][CH2:27][CH3:28].ON1C2N=CC=CC=2N=N1.C(Cl)CCl.CN1CCOCC1>O.CS(C)=O>[CH3:29][C:23]1[NH:22][C:21](=[O:30])[C:20]([CH2:19][NH:18][C:15]([C:8]2[C:7]3[CH:6]=[CH:5][NH:4][C:12]=3[C:11]([O:13][CH3:14])=[CH:10][CH:9]=2)=[O:17])=[C:25]([CH2:26][CH2:27][CH3:28])[CH:24]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateHCID 674686821-(1-Methylethyl)-7-(methyloxy)-1H-indole-4-carboxylic acid

Product 1

HCID 131732560HCID 131732560, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Added 1-(1-methylethyl)-7-(methyloxy)-1H-indole-4-carboxylic acid (160 mg, 0.686 mmol), 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (186 mg, 0.857 mmol), 1-hydroxy-7-azabenzotriazole (187 mg, 1.372 mmol), EDC (263 mg, 1.372 mmol) and N-methylmorpholine (0.302 mL, 2.74 mmol) to DMSO (10 mL) and stirred mixture at RT for 16 h. Added 25 ml of water and stirred for 10 minutes. Filtered off solids and dried in vacuo. The solids were purified by column chromatography (Biotage; 0% to 15% gradient MeOH:DCM; 10 g-HP-silica gel column) to give 165 mg of 141-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-7-(methyloxy)-1H-indole-4-carboxamide. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.01 (t, 3 H), 1.45 (d, J=6.57 Hz, 6 H), 1.63 (m, J=7.45, 7.45, 7.45, 7.45, 7.33 Hz, 2 H), 2.24 (s, 3 H), 2.74 (t, J=7.58 Hz, 2 H), 3.96 (s, 3 H), 4.64 (br. s., 2 H), 5.45 (quin, J=6.63 Hz, 1 H), 5.97 (s, 1 H), 6.62 (d, J=8.08 Hz, 1 H), 6.94 (d, J=3.28 Hz, 1 H), 7.24 (d, J=3.28 Hz, 1 H), 7.53 (d, J=8.08 Hz, 1 H), 7.74 (br. s., 1 H), 12.46 (br. s., 1 H). MS(ES) [M+H]+ 395.7.

Workup

  1. stirringstirred for 10 minutes
  2. filtrationFiltered off solids
  3. customdried in vacuo
  4. customThe solids were purified by column chromatography (Biotage; 0% to 15% gradient MeOH:DCM; 10 g-HP-silica gel column)

Sources & evidence

ORD record
ord-c57687e6a9f642368ceb82ff9c1c4489
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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