Sodium Bicarbonate → Methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}-1-oxidopyridin-3-yl)acetate

HRID 1713878노트

반응식

HRID 1713878 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:15])=[N:11][N:10]=1.Cl[C:24]1[N+:29]([O-:30])=[CH:28][C:27]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>CC(O)(CC)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:13][C:12]([C:14]([NH:16][CH:17]2[CH2:18][CH2:19][N:20]([C:24]3[N+:29]([O-:30])=[CH:28][C:27]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:26][CH:25]=3)[CH2:21][CH2:22]2)=[O:15])=[N:11][N:10]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 59464117HCID 59464117, 화합물HCID 594641305-[(2-fluorophenyl)amino]-N-piperidin-4-yl-1,3,4-oxadiazole-2-carboxamide2회

생성물 1

HCID 59619585Methyl (6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}-1-oxidopyridin-3-yl)acetate수율 32.2%

시약·촉매·용매 1

HCID 64052-Methyl-2-butanol용매

실험 절차

5-[(2-Fluorophenyl)amino]-N-piperidin-4-yl-1,3,4-oxadiazole-2-carboxamide (Intermediate 101) (100 mg, 0.33 mmol) and methyl (6-chloro-1-oxidopyridin-3-yl)acetate (67 mg, 0.33 mmol) were heated with sodium hydrogen carbonate (56 mg, 0.66 mmol) in 2-methyl-2-butanol (4 mL) at 100° C. for 22 h. The reaction mixture was concentrated by evaporation and the residue was dissolved in DMSO then filtered and purified by preparative HPLC to give the title compound (50 mg, 32%) as a gum; 1H NMR δ 1.94-1.74 (m, 4H), 2.58-2.43 (m, 2H), 2.95-2.84 (m, 2H), 3.65 (s, 3H), 4.07-3.93 (m, 3H), 7.21-7.12 (m, 2H), 7.35-7.23 (m, 2H), 7.45-7.40 (m, 1H), 8.06-7.98 (m, 1H), 8.25-8.20 (m, 1H), 9.13 (d, 1H), 10.64 (s, 1H); MS m/e MH+ 471.

후처리

  1. concentrationThe reaction mixture was concentrated by evaporation
  2. dissolutionthe residue was dissolved in DMSO
  3. filtrationthen filtered
  4. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-b3ae287a4061430fad69a3356a529267
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795283B2

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