Tetrahydrofuran → 2-[4-[[2-(3-Chlorophenyl)-5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl]amino]phenyl]-N-cyano-acetamide

HRID 1509065ノート

反応式

HRID 1509065 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]([NH:28][C:29]#[N:30])=[O:27])=[CH:21][CH:20]=3)[C:11]3S[CH2:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.O[O:32][S:33]([O-:35])=O.[K+].C1COCC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([CH2:25][C:26]([NH:28][C:29]#[N:30])=[O:27])=[CH:23][CH:24]=3)[C:11]3[S:33](=[O:35])(=[O:32])[CH2:16][CH2:15][CH2:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 901117042-[4-[[2-(3-Chlorophenyl)-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl]amino]phenyl]-N-cyano-acetamide

生成物 1

HCID 901115792-[4-[[2-(3-Chlorophenyl)-5,5-dioxo-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl]amino]phenyl]-N-cyano-acetamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 18-mL vial was charged with 2-[4-[[2-(3-Chlorophenyl)-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl]amino]phenyl]-N-cyano-acetamide (19 mg, 0.044 mmol, 1 eq.), oxone (55 mg, 0.18 mmol, 4 eq.), THF (3 ml) and water (3 ml). The clear solution was stirred at room temperature overnight. The volatile material was removed under reduced pressure and the residue was treated with sodium bicarbonate solution. Solid was collected by filtration and washed with water. After drying, the title compound was obtained as a white solid (11 mg, 53% yield). MW=467.93. 1H NMR (400 MHz, methanol-d4) δ 8.34 (s, 1H), 8.25 (d, J=7.6 Hz, 1H), 7.60 (d, J=8.0 Hz, 2H), 7.49 (m, 2H), 7.39 (d, J=8.0 Hz, 2H), 3.61 (t, J=4.8 Hz, 2H), 3.56 (s, 2H), 3.13 (t, J=6.4 Hz, 2H), 2.54 (m, 2H).

後処理

  1. customThe volatile material was removed under reduced pressure
  2. additionthe residue was treated with sodium bicarbonate solution
  3. filtrationSolid was collected by filtration
  4. washwashed with water
  5. customAfter drying

出典と根拠

ORDレコード
ord-bb129bf909bb43f5a67dc48883ee4626
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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