1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → rac-[1-({[2,5-Dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic Acid tert-butyl Ester

HRID 1486291ノート

反応式

HRID 1486291 の反応式
[CH3:1][C:2]1[C:17]([C:18]([OH:20])=O)=[C:5]2[CH:6]=[C:7]([CH3:16])[CH:8]=[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[N:4]2[N:3]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[C:42]([O:46][C:47](=[O:56])[NH:48][C:49]([CH3:55])([CH2:52][CH2:53][CH3:54])[CH2:50][NH2:51])([CH3:45])([CH3:44])[CH3:43].C(N(CC)C(C)C)(C)C>O1CCCC1>[C:42]([O:46][C:47](=[O:56])[NH:48][C:49]([CH3:55])([CH2:52][CH2:53][CH3:54])[CH2:50][NH:51][C:18]([C:17]1[C:2]([CH3:1])=[N:3][N:4]2[C:9]([O:10][CH2:11][CH2:12][CH:13]([CH3:14])[CH3:15])=[CH:8][C:7]([CH3:16])=[CH:6][C:5]=12)=[O:20])([CH3:45])([CH3:44])[CH3:43]

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 84723920rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamateHCID 1178597002,5-Dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridine-3-carboxylic Acid

生成物 1

HCID 121434556rac-[1-({[2,5-Dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridin-3-yl]carbonyl}amino)-2-methylpentan-2-yl]carbamic Acid tert-butyl Ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 45 mg (0.163 mmol) of 2,5-dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridine-3-carboxylic acid from Example 8A in 3 ml of tetrahydrofuran was admixed with 30 mg (0.177 mmol) of 1-hydroxybenzotriazole and 30 mg (0.177 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide. The resulting solution was stirred at room temperature for 15 min, and then 45.7 mg (0.212 mmol) of rac-(1-amino-2-methylpentan-2-yl)carbamic acid tert-butyl ester from Example 152A were added, followed by 0.85 ml (0.212 mmol) of N,N-diisopropylethylamine. The mixture was stirred at room temperature for a further 18 h. The solvent was drawn off under reduced pressure and the residue was partitioned between ethyl acetate (10 ml) and water (10 ml). The organic phase was removed and washed with water and aqueous sodium chloride solution, dried with a phase separation cartridge and dried further under reduced pressure, which gave 80 mg (61% of theory, 54% pure) of the target compound.

後処理

  1. stirringThe mixture was stirred at room temperature for a further 18 h
  2. customthe residue was partitioned between ethyl acetate (10 ml) and water (10 ml)
  3. customThe organic phase was removed
  4. washwashed with water and aqueous sodium chloride solution
  5. customdried with a phase separation cartridge
  6. customdried further under reduced pressure, which
  7. customgave 80 mg (61% of theory, 54% pure) of the target compound

出典と根拠

ORDレコード
ord-a6e579842a714d4690ce03a149ad595d
出典データセット
uspto-grants-2016_08
特許番号
US09422285B2

反応ノート

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