1,2-Dichloroethane → HCID 66604406, compound

HRID 2410802Notes

Reaction equation

HRID 2410802 reaction equation
C[N:2]([CH:4]=[O:5])C.[CH:6]([O:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[N:24]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:22]=[C:21](C(O)=O)[C:17]=3[NH:18][C:19]=2[CH:20]=1)=[O:11])([CH3:8])[CH3:7].C(Cl)CCl.O.ON1C2C=CC=CC=2N=N1>O>[C:4]([C:21]1[C:17]2[NH:18][C:19]3[CH:20]=[C:12]([C:10]([O:9][CH:6]([CH3:8])[CH3:7])=[O:11])[CH:13]=[CH:14][C:15]=3[C:16]=2[N:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:22]=1)(=[O:5])[NH2:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66605036HCID 66605036, compound

Product 1

HCID 66604406HCID 66604406, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dry DMF (10 mL) was added to a mixture of 7-(isopropoxycarbonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylic acid (0.95 g, 2.54 mmol), NH4C1 (0.41 g, 7.6 mmol), EDC (1.46 g, 7.61 mmol), and 1-hydroxybenzotriazole hydrate (1.03 g, 7.61 mmol). After stirring for a few minutes, TEA (1.06 mL, 7.61 mmol) was added and the reaction left stirred overnight. It was diluted with water (200 ml) and the precipitate was collected by filtration, washed with water and dried to leave isopropyl 4-carbamoyl-2-phenyl-5H-pyrido[3,2-b]indole-7-carboxylate (0.925 g, 2.28 mmol, 90% yield) as a yellow solid. MS (ESI) m/z 374.04 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.89 (1H, s), 8.66 (1H, br. s.), 8.54 (1H, s), 8.46 (1H, s), 8.38 (1H, d, J=8.24 Hz), 8.33 (2H, d, J=7.32 Hz), 7.92-7.99 (1H, m), 7.88 (1H, dd, J=8.24, 1.22 Hz), 7.57 (2H, t, J=7.63 Hz), 7.46 (1H, t, J=7.32 Hz), 5.22 (1H, dt, J=12.51, 6.26 Hz), 1.39 (6H, d, J=6.41 Hz).

Workup

  1. waitthe reaction left
  2. stirringstirred overnight
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-5b77fa3257b0419ab2cdfcc1316ab6c8
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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