Potassium Phosphate, Tribasic → 2-[7-(3-dimethylaminomethylphenyl)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide

HRID 1157468ノート

反応式

HRID 1157468 の反応式
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:27])[N:7]([CH2:20][C:21]([NH:23][CH:24]([CH3:26])[CH3:25])=[O:22])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:28][N:29]([CH3:46])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.O>[CH3:28][N:29]([CH2:30][C:31]1[CH:32]=[C:33]([C:2]2[CH:11]=[C:10]3[C:5]([C:6](=[O:27])[N:7]([CH2:20][C:21]([NH:23][CH:24]([CH3:26])[CH3:25])=[O:22])[C:8]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=4)=[N:9]3)=[CH:4][CH:3]=2)[CH:34]=[CH:35][CH:36]=1)[CH3:46]

参加物

5

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 38036203-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol esterHCID 685217262-[7-chloro-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide

生成物 1

HCID 595117992-[7-(3-dimethylaminomethylphenyl)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide

試薬・触媒・溶媒 1

HCID 21962138N,N-Dimethylformamide--water (1/1)溶媒

反応条件

温度
80 °C

実験手順

An oven dried flask was charged with 2-[7-chloro-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (INTERMEDIATE IV.11) (38.5 mg, 0.10 mmol), dimethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amine (INTERMEDIATE XI.1) (40 mg, 0.15 mmol) and K3PO4(69 mg, 0.33 mmol) followed by mixture of DMF: H2O (4:1, 5 mL) and purged with argon for a minimum of 10 minutes. CombiPhos™-Pd catalyst (CombiPhos Catalysts Inc., Princeton, N.J.) (1 mole %) was added and the mixture was heated at 80° C. for 18 h. The solvent was removed under vacuum and the residue was dissolved in methanol, filtered and purified by preparative HPLC to give 2-[7-(3-dimethylaminomethylphenyl)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (EXAMPLE 8a) as a colorless oil.

後処理

  1. customAn oven dried flask
  2. custompurged with argon for a minimum of 10 minutes
  3. additionCombiPhos™-Pd catalyst (CombiPhos Catalysts Inc., Princeton, N.J.) (1 mole %) was added
  4. customThe solvent was removed under vacuum
  5. dissolutionthe residue was dissolved in methanol
  6. filtrationfiltered
  7. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-895a6e67dbd540b99c1dbb84d9324cde
出典データセット
uspto-grants-2010_10
特許番号
US07807686B2

反応ノート

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