Isopropylamine → 4-Chloro-N-isopropyl-pyridine-2-carboxamide

HRID 626583ノート

反応式

HRID 626583 の反応式
[CH:1]([NH2:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl.[Cl:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22](Cl)=[O:23])[CH:17]=1>CO.C1COCC1.CCOC(C)=O>[Cl:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:23])[CH:17]=1

参加物

7

反応物 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 223972704-Chloropyridine-2-carbonyl chloride--hydrogen chloride (1/1)

生成物 1

HCID 228320834-Chloro-N-isopropyl-pyridine-2-carboxamide収率 90%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A 0° C. solution of isopropylamine (0.971 mL, 11.30 mmol) and DIEA (1.973 mL, 11.30 mmol) in MeOH (10 mL) and THF (5 mL) was treated with 4-chloropicolinoyl chloride hydrochloride (0.8 g, 3.77 mmol) in one portion, warmed to RT and stirred for 2 h. The mixture was diluted with EtOAc, washed with satd. NaHCO3, then brine and the organic layer was dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (EtOAc/Hex) to afford 4-chloro-N-isopropylpicolinamide (0.67 g, 90%). 1H NMR (400 MHz, DMSO-d6): δ 8.60 (d, J=5.3 Hz, 1H), 8.56 (d, J=8.4 Hz, 1H), 8.00 (d, J=2.2 Hz, 1H), 7.75 (dd, J=5.3, 2.1 Hz, 1H), 4.10-4.09 (m, 1H), 1.17 (d, J=6.6 Hz, 6H); MS (ESI) m/z: 199.1 (M+H+).

後処理

  1. washwashed with satd
  2. dry with materialNaHCO3, then brine and the organic layer was dried over Na2SO4
  3. concentrationconcentrated to dryness
  4. custompurified by silica gel chromatography (EtOAc/Hex)

出典と根拠

ORDレコード
ord-9d5473b8577f4a20bb849a509eb50305
出典データセット
uspto-grants-2016_04
特許番号
US09309224B2

反応ノート

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