p-Toluenesulfonic acid → 1-(Chloromethyl)-N-(2-hydroxyethyl)-3-[(E)-4-methoxycinnamoyl]-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

HRID 2238381Notes

Reaction equation

HRID 2238381 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([S:16]([NH:19][CH2:20][CH2:21][OH:22])(=[O:18])=[O:17])=[CH:15][C:9]=3[C:8]([N+:23]([O-:25])=[O:24])=[CH:7][C:6]=2[NH:5][CH2:4]1.[CH3:26][O:27][C:28]1[CH:38]=[CH:37][C:31](/[CH:32]=[CH:33]/[C:34](O)=[O:35])=[CH:30][CH:29]=1.CCN=C=NCCCN(C)C.CC1C=CC(S(O)(=O)=O)=CC=1>CO.Cl.O.CC(N(C)C)=O>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([S:16]([NH:19][CH2:20][CH2:21][OH:22])(=[O:17])=[O:18])=[CH:15][C:9]=3[C:8]([N+:23]([O-:25])=[O:24])=[CH:7][C:6]=2[N:5]([C:34](=[O:35])/[CH:33]=[CH:32]/[C:31]2[CH:37]=[CH:38][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)[CH2:4]1

Participants

8

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6994144-Methoxycinnamic AcidHCID 686939191-(chloromethyl)-N-(2-hydroxyethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

Product 1

HCID 115195861-(Chloromethyl)-N-(2-hydroxyethyl)-3-[(E)-4-methoxycinnamoyl]-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamideYield 65.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 31374DimethylacetamideSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

(Scheme C). Amine 121 (75 mg, 0.19 mmol) was dissolved in MeOH/HCl(g) at room temperature and the solution was evaporated to dryness under reduced pressure. (E)-4-methoxycinnamic acid (41 mg, 0.23 mmol), EDCI (149 mg, 0.78 mmol), anhydrous TsOH (30 mg, 0.17 mmol) and dry DMA (3 mL) were then added and the mixture was sired at room temperature for 2 h. The mixture was poured into water and the precipitate was collected, washed with water, dried and dissolved in the minimum volume of DMW at room temperature. The solution was diluted with EtOAc, filtered and then diluted with hexane and refrigerated to give 37 (68 mg, 64%): mp 250-251° C.; 1H NMR [(CD3)2SO)] δ 9.35 (s, 1H), 8.83 (d, J=1.6 Hz, 1H), 8.38 (d, J=8.9 Hz, 1H) 8.00 (dd, J=8.9, 1.7 Hz, 1H), 7.90 (t, J=5.8 Hz, 1H), 7.80 (d, J=8.8 Hz, 2H), 7.74 (d, J=15.3 Hz, 1H), 7.10 (d, J=15.3 z, 1H), 7.03 (d, J=8.81 Hz, 2H), 4.72-4.48 (m, 4 H), 4.13-4.06 (m, 2H), 3.83 (s, 3H), 3.38 (q, J=6.0 Hz, 2H), 2.87 (q, J=6.1 Hz, 2H). Anal. (C25H24ClN3O7S) C, H, N.

Workup

  1. customthe solution was evaporated to dryness under reduced pressure
  2. customthe precipitate was collected
  3. washwashed with water
  4. customdried
  5. dissolutiondissolved in the minimum volume of DMW at room temperature
  6. additionThe solution was diluted with EtOAc
  7. filtrationfiltered
  8. additiondiluted with hexane

Sources & evidence

ORD record
ord-9c7104afe20d48db8113b17823042fb7
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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