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

HRID 2238381
ノート
印刷プレビュー

反応式

HRID 2238381 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒HCID 21893726Hydrochloride methanol溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-9c7104afe20d48db8113b17823042fb7
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07718688B2

反応ノート

読み込み中…

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