Veratric Acid → ethyl 3-(7-{5-[3,4-bis(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate

HRID 1512776노트

반응식

HRID 1512776 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.O[NH:36]/[C:37](=[N:54]\[H])/[C:38]1[CH:39]=[CH:40][CH:41]=[C:42]2[C:46]=1[NH:45][CH:44]=[C:43]2[CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[O:8][N:54]=[C:37]([C:38]3[CH:39]=[CH:40][CH:41]=[C:42]4[C:46]=3[NH:45][CH:44]=[C:43]4[CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[N:36]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

참가 물질

7

반응물 5

HCID 7121Veratric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724141Tetrabutylammonium FluorideHCID 178506492HCID 178506492, 화합물

생성물 1

HCID 59146185ethyl 3-(7-{5-[3,4-bis(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3,4-bis(methyloxy)benzoic acid (547 mg) in tetrahydrofuran (15 mL) stirred at room temp was added EDCI (767 mg) and HOBT (613 mg). The reaction mixture was stirred at room temperature for 2 h. Then ethyl 3-{7-[(Z)-(hydroxyamino)(imino)methyl]-1H-indol-3-yl}propanoate (D35) (551 mg) was added. The reaction mixture was stirred at 60° C. for 2 h, and then TBAF (2092 mg) was added. The reaction vessel was sealed and heated in Biotage Initiator using initial normal to 130° C. for 3 h. After cooling the reaction, the solvent was removed. Water (90 mL) and ethanol (30 mL) was added to the residue, a yellow solid was formed, filtered and dried in vacuo to gave the product ethyl 3-(7-{5-[3,4-bis(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indol-3-yl)propanoate (D67) (658 mg). δH (CDCl3, 400 MHz): 1.27 (3H, t), 2.76 (2H, t), 3.18 (2H, t), 4.01 (3H, s), 4.13 (3H, s), 4.16 (2H, q), 7.04 (1H, d), 7.20 (1H, d), 7.29 (1H, t), 7.74 (1H, d), 7.81 (1H, d), 7.90 (1H, dd), 8.14 (1H, dd), 9.63 (1H, s). MS (ES): C23H23N3O5 requires 421. found 422.2 (M+H+).

후처리

  1. stirringThe reaction mixture was stirred at 60° C. for 2 h
  2. customThe reaction vessel was sealed
  3. temperatureheated in Biotage Initiator
  4. customnormal to 130° C.
  5. customfor 3 h
  6. temperatureAfter cooling
  7. customthe reaction
  8. customthe solvent was removed
  9. additionWater (90 mL) and ethanol (30 mL) was added to the residue
  10. customa yellow solid was formed
  11. filtrationfiltered
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-40e958bfb6684e7b9063d913a32191dd
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217028B2

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