1,2-Dichloroethane → 3-(3-Methoxyphenyl)-7-(4-morpholinylcarbonyl)-9h-carbazole-1-carboxamide

HRID 2410673Notes

Reaction equation

HRID 2410673 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17](O)=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C>C1COCC1.C(Cl)Cl.CO>[CH3:27][O:26][C:22]1[CH:21]=[C:20]([C:6]2[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:16]3[NH:15][C:14]4[C:9]([C:8]=3[CH:7]=2)=[CH:10][CH:11]=[C:12]([C:17]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:18])[CH:13]=4)[CH:25]=[CH:24][CH:23]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 666057668-carbamoyl-6-(3-methoxyphenyl)-9H-carbazole-2-carboxylic acid

Product 1

HCID 666040453-(3-Methoxyphenyl)-7-(4-morpholinylcarbonyl)-9h-carbazole-1-carboxamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-carbamoyl-6-(3-methoxyphenyl)-9H-carbazole-2-carboxylic acid (36 mg, 0.100 mmol), morpholine (17 mg, 0.2 mmol), EDC (23 mg, 0.12 mmol), HOBt (18 mg, 0.12 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.035 mL, 0.2 mmol) in a mixture of THF (5 mL) and CH2Cl2 (1 mL) was stirred at room temperature overnight. This was diluted with MeOH and the product was isolated by preparative HPLC (100×30 mm Luna C18 column, flow rate 42 ml permin, gradient elution starting with A:B=90:10 and ending with A:B=30:70 [A=10 mM NH4OAc in 5% aqueous acetonitrile; B=10 mM NH4OAc in 95% aqueous acetonitrile] over 20 min) followed by removal of the solvents. This afforded 29 mg of 3-(3-methoxyphenyl)-7-(morpholine-4-carbonyl)-9H-carbazole 1-carboxamide as a solid. MS (ESI) m/z 430.2 (M+H). 1H NMR (MeOD) δ ppm 8.42 (1H, s), 8.13 (1H, d, J=7.94 Hz), 8.05 (1H, s), 7.57 (1H, s), 7.32-7.41 (2H, m), 7.29 (1H, d, J=7.63 Hz), 7.21-7.26 (1H, m), 6.85-6.93 (1H, m), 3.88 (3H, s), 3.43-3.84 (8H, m).

Workup

  1. customthe product was isolated by preparative HPLC (
  2. wash100×30 mm Luna C18 column, flow rate 42 ml permin, gradient elution
  3. customB=10 mM NH4OAc in 95% aqueous acetonitrile] over 20 min) followed by removal of the solvents

Sources & evidence

ORD record
ord-3672a2fe174d421791bcc4e3d67411c3
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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