Dimethylformamide → HCID 68008851, 화합물

HRID 1429083노트

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HRID 1429083 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([OH:28])[CH2:27][C@H:21]2[C:20](=[O:29])[NH:19][C@:18]2([C:31]([OH:33])=[O:32])[CH2:30][C@H:17]2[CH2:16][C:15]([F:35])([F:34])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:37]1[C:46]([CH2:47][CH3:48])=[N:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]=1.CN(C=O)C.CCC([O-])(C)C.[Na+]>CC#N.Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:37]3[C:46]([CH2:47][CH3:48])=[N:45][C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:38]=3)[CH2:27][C@H:21]2[C:20](=[O:29])[NH:19][C@:18]2([C:31]([OH:33])=[O:32])[CH2:30][C@H:17]2[CH2:16][C:15]([F:35])([F:34])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 2733478Sodium 2-methylbutan-2-olate2회HCID 27795362-Chloro-3-ethylquinoxaline2회HCID 68008615HCID 68008615, 화합물

생성물 1

HCID 68008851HCID 68008851, 화합물수율 57.5%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6342Acetonitrile용매

실험 절차

To (2R,6S,13aS,14aR,16aS)-6-(tert-butoxycarbonylamino)-12,12-difluoro-2-hydroxy-5,16-dioxooctadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylic acid (Example 7j, 87.4 mg, 0.174 mmol) was added 2-chloro-3-ethylquinoxaline (47.7 mg, 0.247 mmol) and DMF (868 μl). To this solution was added sodium tert-pentoxide (48.9 mg, 0.444 mmol) at room temperature, and the mixture turned dark purple (slightly exothermic). The reaction mixture was stirred at room temperature for 17 h. Additional 2-chloro-3-ethylquinoxaline (18.1 mg, 0.094 mmol) and sodium tert-pentoxide (24.2 mg, 0.202 mmol) were added, and the reaction mixture was stirred for 22 h. The reaction mixture was diluted with CH3CN and neutralized with HCl (1 N, 0.7 ml) and evaporated under reduced pressure. The residue was purified by reverse phase HPLC (CH3CN/H2O (0.1%TFA), gradient=20/80-85/15) to provide the title compound as a light brown solid, (2R,6S,13aS,14aR,16aS)-6-(tert-butoxycarbonylamino)-2-(3-ethylquinoxalin-2-yloxy)-12,12-difluoro-5,16-dioxooctadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylic acid (66 mg, 57% yield).

후처리

  1. stirringthe reaction mixture was stirred for 22 h
  2. customevaporated under reduced pressure
  3. customThe residue was purified by reverse phase HPLC (CH3CN/H2O (0.1%TFA), gradient=20/80-85/15)

출처 및 근거

ORD 기록
ord-2145715a38d24e559088cc15146b3087
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937041B2

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