Dicyclohexylcarbodiimide → 6-fluoro-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}-2,3,4,9-tetrahydro-1H-carbazole-2-carboxamide

HRID 1593605노트

반응식

HRID 1593605 반응식
Cl.[CH3:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[O:16][CH2:15][C@H:14]([CH2:17][NH2:18])[O:13][C:9]3=2)[N:4]=1.[F:19][C:20]1[CH:21]=[C:22]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]1[CH2:27][CH:26]([C:33](O)=[O:34])[CH2:25][CH2:24][C:23]2=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>O1CCCC1.C(N(CC)CC)C>[F:19][C:20]1[CH:21]=[C:22]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28]1[CH2:27][CH:26]([C:33]([NH:18][CH2:17][C@@H:14]3[O:13][C:9]4=[C:10]5[C:5](=[CH:6][CH:7]=[C:8]4[O:16][CH2:15]3)[N:4]=[C:3]([CH3:2])[CH:12]=[CH:11]5)=[O:34])[CH2:25][CH2:24][C:23]2=1

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 214527086-Fluoro-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylic acidHCID 69469039[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methylamine hydrochloride

생성물 1

HCID 866076466-fluoro-N-{[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl}-2,3,4,9-tetrahydro-1H-carbazole-2-carboxamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

[(2S)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methylamine hydrochloride (360 mg, 1.35 mmol) and compound I were suspended in anhydrous tetrahydrofuran (THF) containing triethylamine (1.8 mL) and HOBT (54 mg) with stirring for 15 min. The coupling reagent, DCC (300 mg) was added and stirring was continued overnight. The reaction mixture was filtered and the filtrate was diluted with water and extracted with ether. The ether layers were combined, dried (MgSO4), and evaporated under reduced pressure to give a residue which was purified by flash chromatography on silica gel eluting with 1-2% methanol in methylene chloride to give the intermediate II (240 mg) as a white solid. mp 262-267° C.; MS (ES) m/z 444.3.

후처리

  1. stirringstirring
  2. waitwas continued overnight
  3. filtrationThe reaction mixture was filtered
  4. additionthe filtrate was diluted with water
  5. extractionextracted with ether
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customto give a residue which
  9. customwas purified by flash chromatography on silica gel eluting with 1-2% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-b2606a0f859249e08d0688ad35c716a6
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297704B2

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