Diisopropylethylamine → N-{5-[(cyclopropylcarbonyl)amino]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide

HRID 1921294ノート

反応式

HRID 1921294 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16]([OH:18])=O)=[CH:10]1.[NH2:19][C:20]1[CH:21]=[C:22]([NH:27][C:28]([CH:30]2[CH2:32][CH2:31]2)=[O:29])[CH:23]=[CH:24][C:25]=1[CH3:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH:30]1([C:28]([NH:27][C:22]2[CH:23]=[CH:24][C:25]([CH3:26])=[C:20]([NH:19][C:16]([C:11]3[CH:12]=[CH:13][C:14](=[O:15])[N:9]([C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[CH:10]=3)=[O:18])[CH:21]=2)=[O:29])[CH2:31][CH2:32]1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24693537N-(3-amino-4-methylphenyl)cyclopropanecarboxamideHCID 655011901-(2,6-Dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

生成物 1

HCID 59234680N-{5-[(cyclopropylcarbonyl)amino]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide収率 51.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid (30 mg) in DMF (0.6 mL) were added N-(3-amino-4-methylphenyl)cyclopropanecarboxamide (30 mg), HATU (60 mg) and iPr2NEt (62 mg) successively, and the mixture was stirred under a nitrogen atmosphere at room temperature for 16 hr. The reaction mixture was diluted with EtOAc (3 mL), and the resulting mixture was washed with 1 M HCl (3 mL×2), saturated aqueous NaHCO3 (3 mL×2) and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was triturated with 10% MeOH in CH2Cl2, and the precipitates produced were collected by filtration to give N-{5-[(cyclopropylcarbonyl)amino]-2-methylphenyl}-1-(2,6-dichlorophenyl)-6-oxo-1,6-dihydro-3-pyridinecarboxamide (25 mg).

後処理

  1. washthe resulting mixture was washed with 1 M HCl (3 mL×2), saturated aqueous NaHCO3 (3 mL×2) and brine successively
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was triturated with 10% MeOH in CH2Cl2
  5. customthe precipitates produced
  6. filtrationwere collected by filtration

出典と根拠

ORDレコード
ord-b399c39ab62a47ada02cf5fdd4ab66cd
出典データセット
uspto-grants-2012_05
特許番号
US08173684B2

反応ノート

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