Diisopropylethylamine → Methyl 4-[(6-chloro-3-methyl-pyridine-2-carbonyl)amino]-3,5-dimethyl-benzoate

HRID 239916

反応式

HRID 239916 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O-:10])=O)[CH:5]=[CH:4][CH:3]=1.[K+].O=[C:13]1N([ClH]P([ClH]N2CCOC2=O)=O)CCO1.[NH2:28][C:29]1[C:38]([CH3:39])=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=1[CH3:40].C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:28][C:29]2[C:30]([CH3:40])=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][C:38]=2[CH3:39])=[O:10])[C:5]([CH3:13])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 11030398Benzoic acid, 4-amino-3,5-dimethyl-, methyl esterHCID 86707310Potassium 6-chloropyridine-2-carboxylate

生成物 1

HCID 86707309Methyl 4-[(6-chloro-3-methyl-pyridine-2-carbonyl)amino]-3,5-dimethyl-benzoate収率 86.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of potassium 6-chloropyridine-2-carboxylate (52 g, 265.8 mmoles) in dimethylformamide (676 mL) is added bis(2-oxo-3-oxazolidinyl)phosphonic chloride (115 g, 451.8 mmoles). The mixture is stirred at ambient temperature for 30 minutes. Methyl 4-amino-3,5-dimethyl-benzoate (42.9 g, 239.2 mmoles, see preparation 12) and diisopropylethylamine (115.9 mL, 664.5 mmoles) are added. The reaction is stirred at ambient temperature for 16 hours. The mixture is then poured into water (2000 mL) and is stirred for 30 minutes. The resulting solid is filtered and dried under reduced pressure at 45° C. The dry material is triturated with hexane (1400 mL) over 2 hours. The solid is filtered and dried under vacuum to give the title compound (69 g, 78%) as a white solid. Mass spectrum (m/z): 333.05 (M+1). 1H NMR (300 MHz, DMSO): 10.16 (s, 1H), 7.89 (d, J=8.2 Hz, 1H), 7.73 (s, 2H), 7.63 (d, J=8.2 Hz, 1H), 3.85 (s, 3H), 2.49 (s, 3H), 2.28 (s, 6H).

後処理

  1. stirringThe reaction is stirred at ambient temperature for 16 hours
  2. stirringis stirred for 30 minutes
  3. filtrationThe resulting solid is filtered
  4. customdried under reduced pressure at 45° C
  5. customThe dry material is triturated with hexane (1400 mL) over 2 hours
  6. filtrationThe solid is filtered
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-f6bb69db1dff4b349f23b9bbba4ba0fb
出典データセット
uspto-grants-2014_02
特許番号
US08642768B2

関連ノート

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