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 1713878ノート

反応式

HRID 1713878 の反応式
[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

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 59464117HCID 59464117、化合物HCID 594641305-[(2-fluorophenyl)amino]-N-piperidin-4-yl-1,3,4-oxadiazole-2-carboxamide2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 64052-Methyl-2-butanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b3ae287a4061430fad69a3356a529267
出典データセット
uspto-grants-2010_09
特許番号
US07795283B2

反応ノート

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