p-Toluenesulfonic acid monohydrate → HCID 59815654、化合物

HRID 499054ノート

反応式

HRID 499054 の反応式
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]CC3C=CC=CC=3)=[CH:16][CH:15]=2)=[N:6][CH:5]=1.O.[C:30]1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(OCC)(=O)C.C(OC)(OC)OC.[Pd]>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[N:10]=[CH:30][N:13]([C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)[C:7]2=[N:6][CH:5]=1)=[O:28]

参加物

7

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 598156466-(4-Benzyloxyphenylamino)-5-nitronicotinic acid methyl ester

生成物 1

HCID 59815654HCID 59815654、化合物

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒HCID 9005Trimethyl orthoformate溶媒

実験手順

To a suspension of XXIV (235 mg, 0.62 mmol) in MeOH (3 mL) and ethyl acetate (3 mL) was added 10% Pd—C (47 mg) under nitrogen atmosphere. The resulting mixture was hydrogenated at rt overnight. The catalyst was removed by filtration under nitrogen and washed with methanol, the filtrate was concentrated under reduced pressure to give a white solid. MS (ES, Pos.): m/z 260 [MH+]. The hydrogenation product was suspended in trimethyl orthoformate (5 mL), and p-toluenesulfonic acid monohydrate (12 mg, 0.062 mmol) was added. The resulting mixture was stirred at rt overnight. The white solid was collected by filtration. MS (ES, Pos.): m/z 270 [MH+]. 1H NMR (CD3OD, 400 MHz): δ=3.99 (s, 3H), 7.00 (d, J=8.8 Hz, 2H), 7.59 (d, J=8.8 Hz, 2H), 8.71 (d, J=1.8 Hz, 1H), 8.72 (s, 1H), 9.05 (d, J=1.8 Hz, 1H).

後処理

  1. customThe catalyst was removed by filtration under nitrogen
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a white solid
  5. filtrationThe white solid was collected by filtration

出典と根拠

ORDレコード
ord-70af0a7279054914964cfe8bacdbc353
出典データセット
uspto-grants-2010_08
特許番号
US07767673B2

反応ノート

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