Diisopropylethylamine → rac-{1-[({5-Cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridin-3-yl}carbonyl)amino]-2-methylpentan-2-yl}carbamic Acid tert-butyl Ester

HRID 1486315ノート

反応式

HRID 1486315 の反応式
ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH:23]1([C:26]2[CH:31]=[C:30]([O:32][CH2:33][C:34]3[C:39]([F:40])=[CH:38][CH:37]=[CH:36][C:35]=3[F:41])[N:29]3[N:42]=[C:43]([CH3:48])[C:44]([C:45](O)=[O:46])=[C:28]3[CH:27]=2)[CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C.[C:58]([O:62][C:63](=[O:72])[NH:64][C:65]([CH3:71])([CH2:68][CH2:69][CH3:70])[CH2:66][NH2:67])([CH3:61])([CH3:60])[CH3:59]>O1CCCC1>[C:58]([O:62][C:63](=[O:72])[NH:64][C:65]([CH3:71])([CH2:68][CH2:69][CH3:70])[CH2:66][NH:67][C:45]([C:44]1[C:43]([CH3:48])=[N:42][N:29]2[C:30]([O:32][CH2:33][C:34]3[C:35]([F:41])=[CH:36][CH:37]=[CH:38][C:39]=3[F:40])=[CH:31][C:26]([CH:23]3[CH2:25][CH2:24]3)=[CH:27][C:28]=12)=[O:46])([CH3:61])([CH3:60])[CH3:59]

参加物

7

反応物 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 84723920rac-tert-Butyl (1-amino-2-methylpentan-2-yl)carbamateHCID 1178596065-Cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

生成物 1

HCID 117864545rac-{1-[({5-Cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[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

76 mg (0.6 mmol) of 1-hydroxy-7-azabenzotriazole and 107 mg (0.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added to a solution of 167 mg (0.5 mmol) of 5-cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid (Example 149A), 244 μl (1.4 mmol) of N,N-diisopropylethylamine and 121 mg (0.6 mmol) of rac-(1-amino-2-methylpentan-2-yl)carbamic acid tert-butyl ester from Example 152A in 5 ml of tetrahydrofuran. The mixture was stirred at room temperature for 18 h and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was removed and washed with water and saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified by chromatography on silica gel (40 g silica gel cartridge, mobile phase: cyclohexane/ethyl acetate, gradient 0% to 100%). This gave 125 mg of the target compound (48% of theory).

後処理

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe organic phase was removed
  4. washwashed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (40 g silica gel cartridge, mobile phase: cyclohexane/ethyl acetate, gradient 0% to 100%)

出典と根拠

ORDレコード
ord-ce52306062f0473eb0dd8b0a47d35e5b
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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