1-Hydroxybenzotriazole → rac-{1-[({7-[(2-Chloro-6-fluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

HRID 1486304ノート

反応式

HRID 1486304 の反応式
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:18])[C:14]([C:15](O)=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:19])[CH:7]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:47]([O:51][C:52](=[O:61])[NH:53][C:54]([CH2:59][NH2:60])([CH3:58])[CH2:55][CH2:56][CH3:57])([CH3:50])([CH3:49])[CH3:48].C(N(CC)C(C)C)(C)C>O1CCCC1>[C:47]([O:51][C:52](=[O:61])[NH:53][C:54]([CH3:58])([CH2:55][CH2:56][CH3:57])[CH2:59][NH:60][C:15]([C:14]1[C:13]([CH3:18])=[N:12][N:11]2[C:6]([O:5][CH2:4][C:3]3[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:2]=3[Cl:1])=[CH:7][C:8]([CH3:19])=[CH:9][C:10]=12)=[O:16])([CH3:48])([CH3:49])[CH3:50]

参加物

7

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 84723920rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamateHCID 1178595577-(2-Chloro-6-fluorobenzyloxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

生成物 1

HCID 117864595rac-{1-[({7-[(2-Chloro-6-fluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 26 mg (0.074 mmol) of 7-(2-chloro-6-fluorobenzyloxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (Example 137A) in 3 ml of tetrahydrofuran was admixed with 17 mg (0.09 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 14 mg (0.09 mmol) of 1-hydroxybenzotriazole, 21 mg (0.096 mmol) of rac-(1-aminomethyl-1-methylbutyl)carbamic acid tert-butyl ester from Example 152A and 0.039 ml (0.222 mmol) of N,N-diisopropylethylamine. The mixture was stirred at room temperature for a further 18 hours. The reaction mixture was then heated to 60° C. for 3 hours. After concentration under reduced pressure, the residue was partitioned between dichloromethane and water. The organic phase was removed and concentrated under reduced pressure, which gave 40 mg (99% yield) of the target compound.

後処理

  1. temperatureThe reaction mixture was then heated to 60° C. for 3 hours
  2. concentrationAfter concentration under reduced pressure
  3. customthe residue was partitioned between dichloromethane and water
  4. customThe organic phase was removed
  5. concentrationconcentrated under reduced pressure, which

出典と根拠

ORDレコード
ord-c8c2640b235d41d3841a2223a691b67e
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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