1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Acetylamino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid amide

HRID 1497798ノート

反応式

HRID 1497798 の反応式
Br[C:2]1[C:3]([CH3:25])=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[C:5]2[N:6]([N:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=2)[CH:7]=1.Cl.N[OH:28].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[N:47]12[CH2:57]CCN=C1CCCCC2.C(N(CC)C(C)C)(C)C>O1CCOCC1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[C:12]([NH:11][C:9]1[N:10]=[C:5]2[C:4]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[C:3]([CH3:25])[C:2]([C:57]([NH2:47])=[O:28])=[CH:7][N:6]2[N:8]=1)(=[O:14])[CH3:13]

参加物

9

反応物 5

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 86708104N-[6-Bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide

生成物 1

HCID 867081092-Acetylamino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid amide収率 34.8%

試薬・触媒・溶媒 3

HCID 98885Molybdenum carbonyl (Mo(CO)6)触媒HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

A mixture of N-[6-bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide (Int. 18, 330 mg, 0.80 mmol), hydroxylamine hydrochloride (112 mg, 1.60 mmol), trans-bis(acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) (38 mg, 0.04 mmol), tri-tert-butylphosphonium tetrafluoroborate, (22 mg, 0.08 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.12 mL, 0.80 mmol), N,N-diisopropylethylamine, (0.28 mL, 1.60 mmol) and molybdenum hexacarbonyl (106 mg, 0.40 mmol) in dioxane (2 mL) was heated at 150° C. for 20 minutes using microwave irradiation. The reaction mixture was cooled and filtered through Celite®. The solvent was concentrated in vacuo and the residue purified by chromatography eluting with a gradient of 0-100% cyclohexane in EtOAc and then with 10% MeOH in EtOAc to afford the title compound as a beige foam (105 mg).

後処理

  1. custommicrowave irradiation
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through Celite®
  4. concentrationThe solvent was concentrated in vacuo
  5. customthe residue purified by chromatography
  6. washeluting with a gradient of 0-100% cyclohexane in EtOAc

出典と根拠

ORDレコード
ord-00761c48217542458ff7d72bb61a0682
出典データセット
uspto-grants-2015_12
特許番号
US09199984B2

反応ノート

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