Acetyl chloride → N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-chlorophenyl)-2,2,2-trifluoroacetamide

HRID 1800628ノート

反応式

HRID 1800628 の反応式
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:25])=[C:16]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH:17]=1)[N:5]=2.[C:26](Cl)(=[O:28])[CH3:27]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(OCC)(=O)C.O>[C:26]([NH:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[CH:14][C:15]([Cl:25])=[C:16]([NH:18][C:19](=[O:24])[C:20]([F:22])([F:21])[F:23])[CH:17]=1)[N:5]=2)(=[O:28])[CH3:27]

参加物

7

反応物 2

HCID 6367Acetyl chlorideHCID 57384282N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide

生成物 1

HCID 86646052N-(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-chlorophenyl)-2,2,2-trifluoroacetamide収率 85%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-{5-[(2-Amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-2-chlorophenyl}-2,2,2-trifluoroacetamide (1.8 g, 4.63 mmol) and N,N-dimethylpyridine-4-amine (566 mg, 4.63 mmol) were dissolved in pyridine (9.25 mL), acetyl chloride (0.658 mL, 9.25 mmol) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate (80 mL)/water (50 mL), and the organic layer was collected, and washed with saturated brine (50 mL). The mixture was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residual solid was crystallized from toluene/diisopropyl ether (1:3), collected by filtration, and dried to give the title compound (1.69 g, 85%) as a pale-yellow solid.

後処理

  1. temperaturecooling
  2. customthe organic layer was collected
  3. washwashed with saturated brine (50 mL)
  4. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residual solid was crystallized from toluene/diisopropyl ether (1:3)
  7. filtrationcollected by filtration
  8. customdried

出典と根拠

ORDレコード
ord-7a8a1ca44c5c46538feebed33705392a
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

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