Ammonia → 1-(Chloromethyl)-3-{5-[2-(dimethylamino)ethoxy]indol-2-carbonyl}-5,7-dinitro-1,2-dihydro-3H-benzo[e]indole

HRID 2238389노트

반응식

HRID 2238389 반응식
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:9]=3[C:8]([N+:19]([O-:21])=[O:20])=[CH:7][C:6]=2[NH:5][CH2:4]1.Cl.[CH3:23][N:24]([CH3:40])[CH2:25][CH2:26][O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32]([C:37](O)=[O:38])=[CH:31]2.CCN=C=NCCCN(C)C.CC1C=CC(S(O)(=O)=O)=CC=1.N.Cl>CC(N(C)C)=O.CO.CCOC(C)=O>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:9]=3[C:8]([N+:19]([O-:21])=[O:20])=[CH:7][C:6]=2[N:5]([C:37]([C:32]2[NH:33][C:34]3[C:30]([CH:31]=2)=[CH:29][C:28]([O:27][CH2:26][CH2:25][N:24]([CH3:40])[CH3:23])=[CH:36][CH:35]=3)=[O:38])[CH2:4]1

참가 물질

10

반응물 6

HCID 222AmmoniaHCID 313Hydrochloric Acid2회HCID 6101p-Toluenesulfonic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 44549399HCID 44549399, 화합물HCID 686908585-[2-(Dimethylamino)ethoxy]indole-2-carboxylic acid hydrochloride

생성물 1

HCID 116852551-(Chloromethyl)-3-{5-[2-(dimethylamino)ethoxy]indol-2-carbonyl}-5,7-dinitro-1,2-dihydro-3H-benzo[e]indole

시약·촉매·용매 3

HCID 887Methanol용매HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

A mixture of amine 135 (100 mg, 0.33 mmol), 5-[2-(dimethylamino)ethoxy]indole-2-carboxylic acid hydrochloride (111 mg, 0.39 mmol), EDCI (249 mg, 1.30 mmol) and anhydrous TsOH (4.0 mg, 0.02 mmol) in dry DMA (8 mL) was stirred at room temperature under N2 for 6 h, then poured into dilute aqueous NH3. The basic mixture was stirred for 1 h, then the precipitate was collected and dissolved in EtOAc (300 mL) at room temperature. The solution was washed with water, dried, and then concentrated to 10 mL under reduced pressure below 30° C. to give crude 9. Treatment of a suspension of the free base in MeOH with HCl(g)/EtOAc, followed by crystallization from MeOH/Me2CO/EtOAc gave 9.HCl (114 mg, 60%) as a yellow solid: mp 263-264° C.; 1H NMR [(CD3)2SO] δ 11.88 (s, 1H), 10.15 (br s, 1H), 9.36 (s, 1H), 9.34 (d, J=2.2 Hz, 1H, 8.48 (d, J=9.3 Hz, 1H), 8.41 (dd, J=9.3, 2.2 Hz, 1H), 7.46 (d, J=8.9 Hz, 1H), 7.26 (s, 2H), 7.03 (dd, J=8.9, 2.3 Hz, 1H), 5.00 (t, J=10.5 Hz, 1H), 4.78-4.65 (m, 2H), 4.36 (t, J=4.9 Hz, 2H), 4.22-4.09 (m, 2H), 3.52 (t, J=4.5 Hz, 2H), 2.80 (s, 6H). Anal. (C26H24ClN5O6.HCl) C, H, N.

후처리

  1. stirringThe basic mixture was stirred for 1 h
  2. customthe precipitate was collected
  3. dissolutiondissolved in EtOAc (300 mL) at room temperature
  4. washThe solution was washed with water
  5. customdried
  6. concentrationconcentrated to 10 mL under reduced pressure below 30° C.
  7. customto give crude 9
  8. customfollowed by crystallization from MeOH/Me2CO/EtOAc
  9. customgave 9

출처 및 근거

ORD 기록
ord-579121c5262a4bd48d4e7f2fb88c52b0
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07718688B2

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