Isobutylamine → [4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methanol

HRID 1798888ノート

反応式

HRID 1798888 の反応式
C([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]2[C:16]3[N:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)C.CC(C)CN.NCC(C)(O)C.B(Br)(Br)Br>ClCCl>[NH2:17][C:9]1[C:8]2[N:18]=[C:5]([CH2:4][OH:3])[N:6]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]=2[C:16]2[N:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

参加物

6

反応物 4

HCID 6558IsobutylamineHCID 25134Boron tribromideHCID 951022-Propanol, 1-amino-2-methyl-HCID 68934983HCID 68934983、化合物

生成物 1

HCID 11601483[4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a chilled solution (ice bath) of 2-(ethoxymethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (2.0 g, 6.69 mmol, prepared according to the general methods of Example 6 using 2-methylpropan-1-amine in lieu of 1-amino-2-methylpropan-2-ol) in dichloromethane (50 mL) was added boron tribromide (20 mL, 1M solution in dichloromethane). The mixture turned light purple and was stirred at ambient temperature for 44 hours. The reaction was quenched with methanol (20 mL) and aqueous hydrochloric acid (6N, 10 mL). After stirring for 4 hours, the pH was adjusted to 10 by the addition of aqueous sodium hydroxide (50%). Dichloromethane (50 mL) was added with stirring and the layers were separated. The aqueous fraction was extracted with chloroform (2×250 mL). The combined organic fractions were concentrated to provide 1.4 g of [4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-2-yl]methanol as a white powder, mp 226-228° C.

後処理

  1. customThe reaction was quenched with methanol (20 mL) and aqueous hydrochloric acid (6N, 10 mL)
  2. stirringAfter stirring for 4 hours
  3. additionthe pH was adjusted to 10 by the addition of aqueous sodium hydroxide (50%)
  4. additionDichloromethane (50 mL) was added
  5. stirringwith stirring
  6. customthe layers were separated
  7. extractionThe aqueous fraction was extracted with chloroform (2×250 mL)
  8. concentrationThe combined organic fractions were concentrated

出典と根拠

ORDレコード
ord-11f4dbb92a984ea3a9b17820d2f4bc82
出典データセット
uspto-grants-2013_01
特許番号
US08343993B2

反応ノート

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