Triethylamine → N-(3-hydroxy-4,4-dimethyl-pentyl)-2-isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide

HRID 1753911ノート

反応式

HRID 1753911 の反応式
[CH:1]([C:4]1[C:9]([C:10]([OH:12])=O)=[C:8]([CH3:13])[CH:7]=[C:6]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[NH2:27][CH2:28][CH2:29][CH:30]([OH:35])[C:31]([CH3:34])([CH3:33])[CH3:32]>O1CCCC1.C(OCC)(=O)C.[Cl-].[NH4+]>[OH:35][CH:30]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:29][CH2:28][NH:27][C:10]([C:9]1[C:4]([CH:1]([CH3:2])[CH3:3])=[N:5][C:6]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:7][C:8]=1[CH3:13])=[O:12]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 552837561-Amino-4,4-dimethylpentan-3-olHCID 708170442-Isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid

生成物 1

HCID 70816831N-(3-hydroxy-4,4-dimethyl-pentyl)-2-isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide収率 49%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a solution of 2-isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid (synthesized similar to the methods described in sections a) to d) of example X1) (1.86 g, 7.05 mmol) in tetrahydrofuran (60 ml) are added triethylamine (2.9 ml, 21.1 mol) and 0-(7-azabenzotriazol-1-yl)N,N,N′,N′-tetramethyluronium hexafluorophosphate (2.69 g, 7.05 mmol). The mixture is stirred for 15 min at RT, before 1-amino-4,4-dimethylpentan-3-ol (1.02 g, 7.76 mmol) is added and stirring is continued for 18 h. After completion of the reaction, the mixture is diluted with ethyl acetate and 10% aqueous ammonium chloride. The organic layer is separated and washed with saturated sodium hydrogencarbonate solution and brine, dried over magnesium sulphate and evaporated to dryness. The crude product is purified by flash chromatography (silica gel, 30% ethyl acetate/cyclohexane) to yield N-(3-hydroxy-4,4-dimethyl-pentyl)-2-isopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid amide (example X5) (1.30 g, 3.44 mmol, 49%). [M+H]+378.3.

後処理

  1. additionis added
  2. customAfter completion of the reaction
  3. customThe organic layer is separated
  4. washwashed with saturated sodium hydrogencarbonate solution and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness
  7. customThe crude product is purified by flash chromatography (silica gel, 30% ethyl acetate/cyclohexane)

出典と根拠

ORDレコード
ord-476ec2f87c58429192542e5934d10674
出典データセット
uspto-grants-2015_10
特許番号
US09168259B2

反応ノート

読み込み中…