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Triethylamine → N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-methylpropanamide

HRID 1265136
ノート
印刷プレビュー

反応式

HRID 1265136 の反応式
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].Cl.[NH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:18]([CH3:20])=[C:17]([CH3:21])[N:16]=[C:15]([NH2:22])[C:14]=2[N:13]=[C:12]1[CH3:23].C(N(CC)CC)C>ClCCl>[NH2:22][C:15]1[C:14]2[N:13]=[C:12]([CH3:23])[N:11]([CH2:10][CH2:9][NH:8][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[C:19]=2[C:18]([CH3:20])=[C:17]([CH3:21])[N:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 219738191-(2-aminoethyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride

生成物 1

HCID 10236412N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-methylpropanamide収率 74.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Isobutyryl chloride (1.3 mL, 12.2 mmol) was added dropwise to a mixture of 1-(2-aminoethyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride (4.0 g of material from Example 24, 12.2 mmol), triethylamine (85 mL, 610 mmol) and dichloromethane (400 mL). After 15 minutes analysis by high performance liquid chromatography indicated that the reaction was complete. The solvents were removed under reduced pressure. The residue was partitioned between chloroform (250 mL) and water (250 mL) containing 10 g of sodium carbonate (pH 12). This mixture was placed in a continuous extractor and extracted with chloroform for 24 hours. The extract was dried over magnesium sulfate and then concentrated under reduced pressure to provide a light yellow oil. The oil was purified by chromatography (silica gel eluting with 85/15 dichloromethane/methanol) to provide 2.63 g of N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-methylpropanamide as a white powder, m.p. 220-222° C.

後処理

  1. customThe solvents were removed under reduced pressure
  2. customThe residue was partitioned between chloroform (250 mL) and water (250 mL)
  3. additioncontaining 10 g of sodium carbonate (pH 12)
  4. extractionextracted with chloroform for 24 hours
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto provide a light yellow oil
  8. customThe oil was purified by chromatography (silica gel eluting with 85/15 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-f6527e28cad94fb6932c171c0c5dc94d
出典データセット
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06545016B1

反応ノート

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