1,2-Dichloroethane → ({3-[7-(4-Fluoro-benzyl)-9-hydroxy-5-methoxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-6-ylsulfanyl]-propionylamino}-methyl)-phosphonic Acid Diethyl Ester

HRID 853633노트

반응식

HRID 853633 반응식
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:19](=[O:20])[C:18]3[C:17]([OH:21])=[C:16]4[C:11]([CH:12]=[CH:13][CH:14]=[N:15]4)=[C:10]([O:22][CH3:23])[C:9]=3[CH:8]2[S:24][CH2:25][CH2:26][C:27]([OH:29])=O)=[CH:4][CH:3]=1.C(O)(=O)C(O)=O.[CH2:38]([O:40][P:41]([CH2:46][NH2:47])(=[O:45])[O:42][CH2:43][CH3:44])[CH3:39].C(Cl)CCl.P(=O)([O-])OCN>C(Cl)Cl>[CH2:38]([O:40][P:41]([CH2:46][NH:47][C:27](=[O:29])[CH2:26][CH2:25][S:24][CH:8]1[C:9]2[C:10]([O:22][CH3:23])=[C:11]3[C:16](=[C:17]([OH:21])[C:18]=2[C:19](=[O:20])[N:7]1[CH2:6][C:5]1[CH:30]=[CH:31][C:2]([F:1])=[CH:3][CH:4]=1)[N:15]=[CH:14][CH:13]=[CH:12]3)(=[O:45])[O:42][CH2:43][CH3:44])[CH3:39]

참가 물질

6

반응물 4

HCID 111,2-Dichloroethane2회HCID 2733594diethyl (aminomethyl)phosphonate oxalate saltHCID 100034673-[[7-[(4-fluorophenyl)methyl]-9-hydroxy-5-methoxy-8-oxo-6H-pyrrolo[3,4-g]quinolin-6-yl]sulfanyl]propanoic acidHCID 178514127HCID 178514127, 화합물

생성물 1

HCID 10483568({3-[7-(4-Fluoro-benzyl)-9-hydroxy-5-methoxy-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-6-ylsulfanyl]-propionylamino}-methyl)-phosphonic Acid Diethyl Ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 24 (15 mg, 0.035 mmol) in 0.35 mL of CH2Cl2 (0.35 mL) was added diethyl(aminomethyl)phosphonate oxalate (27 mg, 0.105 mmol), EDC (20 mg, 0.105 mmol) and TEA (15 μL, 0.105 mmol). The solution was stirred at room temperature for 1 day when the same amount of the aminomethyl phosphonate, EDC and TEA were added. The reaction was stirred for another day when complete conversion of starting materials to the desired product was observed by LCMS. The product 26 was purified by reverse phase HPLC using 5-95% A. Buffer A contained CH3CN-1% HOAc and buffer B was H2O-1% HOAc. 1H NMR (300 MHz, CDCl3) δ 1.33-1.40 (m, 6H), 2.37-2.45 (m, 4H), 3.60-3.72 (m, 2H), 4.05 (s, 3H), 4.06-4.18 (m, 4H), 4.44 (d, 1H, J=15 Hz), 5.33 (d, 1H, J=14 Hz), 5.49 (s, 1H), 6.17 (br s, 1H), 6.98-7.08 (m, 2H), 7.33-7.43 (m, 2H), 7.55-7.63 (m, 1H), 8.50-8.57 (br d, 1H), 8.97 (br s, 1H); 31P (121.4 MHz, CDCl3) δ 22.7; 19F NMR (282.6 MHz, CDCl3) δ 62.6; EI MS (m/z) 590.4 [M−H]−, 614.2 [M+Na].

후처리

  1. additionwere added

출처 및 근거

ORD 기록
ord-3f236d19e45146df80ee5ca44c04116c
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253180B2

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