Hydrochloric Acid → Methyl 1-benzenesulfonyl-7-chloro-3-phenylcarbamoylmethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate

HRID 1439908Notes

Reaction equation

HRID 1439908 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([S:14]([N:17]2[C:25]3[CH:24]=[C:23]([Cl:26])[CH:22]=[C:21]4[CH2:27][CH2:28][CH:29]([CH2:30][C:31]([OH:33])=O)[C:19]([C:20]=34)=[C:18]2[C:34]([O:36][CH3:37])=[O:35])(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C=O)C>[C:8]1([S:14]([N:17]2[C:25]3[CH:24]=[C:23]([Cl:26])[CH:22]=[C:21]4[CH2:27][CH2:28][CH:29]([CH2:30][C:31](=[O:33])[NH:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[C:19]([C:20]=34)=[C:18]2[C:34]([O:36][CH3:37])=[O:35])(=[O:15])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 15337219Methyl 1-benzenesulfonyl-7-chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate

Product 1

HCID 15337220Methyl 1-benzenesulfonyl-7-chloro-3-phenylcarbamoylmethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylateYield 111.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of aniline (27.4 mg, 0.303 mmol), methyl 1-benzenesulfonyl-7-chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate (120 mg, 0.275 mmol), 1-hydroxy-benzotriazole (46 mg, 0.303 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (47 mg, 0.303 mmol) in DMF (2.5 mL) was stirred for 20 h at room temperature, acidified to pH 1 by adding 1N HCl, and extracted with 1:1 toluene/ethyl acetate. The organic layer was washed successively with 1N HCl, water, saturated sodium bicarbonate, water, and brine, dried over magnesium sulfate, and concentrated to give 161 mg of the title compound (quant): 1H NMR (CDCl3) δ7.95 (d, 2H, J=7.3 Hz), 7.90 (s, 1H), 7.85 (s, 1H), 7.58 (t, 1H, J=7.3 Hz), 7.52 (d, 1H, J=8.3 Hz), 7.46 (t, 1H, J=8.3 Hz), 7.30 (t, 1H, J=8.3 Hz), 7.15 (t, 1H, J=7.05 (s, 1H), 3.84 (s, 3H), 3.71 (m, 1H), 2.92 (ddd, 1H, J=17.2, 12.2, 3.6 Hz), 2.80 (md, 1H, J=17.2 Hz), 2.65 (dd, 1H, J=14.2, 4.0 Hz), 2.47 (dd, 1H, J=14.2, 9.6 Hz), 2.19 (md, 1H, J=13.6 Hz), 1.89 (m, 1H).

Workup

  1. extractionextracted with 1:1 toluene/ethyl acetate
  2. washThe organic layer was washed successively with 1N HCl, water, saturated sodium bicarbonate, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e3498c9c34364fa1b845be6eb76e7b62
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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