Diisopropylethylamine → HCID 74222629、化合物

HRID 1624140

反応式

HRID 1624140 の反応式
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([O:10][CH2:11][CH2:12][CH:13]([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15])=[CH:8][C:7]([CH3:22])=[CH:6][N:5]2[C:23]=1[C:24]([OH:26])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:60][C@H:61]([CH2:64][CH2:65][CH2:66][CH3:67])[CH2:62][OH:63]>CN(C=O)C.O>[OH:63][CH2:62][C@H:61]([NH:60][C:24]([C:23]1[N:5]2[CH:6]=[C:7]([CH3:22])[CH:8]=[C:9]([O:10][CH2:11][CH2:12][CH:13]([C:14]([F:16])([F:15])[F:17])[C:18]([F:19])([F:20])[F:21])[C:4]2=[N:3][C:2]=1[CH3:1])=[O:26])[CH2:64][CH2:65][CH2:66][CH3:67]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 6994402(R)-2-Aminohexan-1-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86717934HCID 86717934、化合物

生成物 1

HCID 74222629HCID 74222629、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

150 mg (0.39 mmol) of 2,6-dimethyl-8-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]imidazo[1,2-a]-pyridine-3-carboxylic acid Example 91A and 163 mg (0.43 mmol) of HATU were initially charged in 2.5 ml of DMF. 0.2 ml (1.17 mmol) of N,N-diisopropylethylamine and 50.3 mg (0.43 mmol) of (R)-(−)-2-amino-1-hexanol were then added, and the mixture was stirred at RT overnight. 10 ml of water were added, the reaction solution was extracted twice with 20 ml of ethyl acetate and the combined organic phases were washed with 20 ml of water and with 20 ml of saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. The residue was purified by preparative RP-HPLC (acetonitrile-water+0.1% formic acid), the product fractions were combined and concentrated to dryness and the residue was dissolved in a mixture of 1.5 ml of tert-butanol and 2 ml of water and lyophilized overnight. This gave 42 mg of the target compound (95% pure, 21% of theory).

後処理

  1. extractionthe reaction solution was extracted twice with 20 ml of ethyl acetate
  2. washthe combined organic phases were washed with 20 ml of water and with 20 ml of saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative RP-HPLC (acetonitrile-water+0.1% formic acid)
  7. concentrationconcentrated to dryness
  8. dissolutionthe residue was dissolved in a mixture of 1.5 ml of tert-butanol and 2 ml of water
  9. waitlyophilized overnight

出典と根拠

ORDレコード
ord-0ff0091317c742fa96190b9564869823
出典データセット
uspto-grants-2014_07
特許番号
US08778964B2

関連ノート

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