2-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine → N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide

HRID 1409253ノート

反応式

HRID 1409253 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]2[CH2:9][CH:8]2[C:10](Cl)=[O:11])=[CH:3][CH:2]=1.[CH3:13][C:14]1[CH:29]=[C:17]2[N:18]=[C:19]([NH2:28])[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]2[N:15]=1>N1C=CC=CC=1>[CH3:13][C:14]1[CH:29]=[C:17]2[N:18]=[C:19]([NH:28][C:10]([CH:8]3[CH2:9][CH:7]3[C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[O:11])[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:16]2[N:15]=1

参加物

4

反応物 2

HCID 582071812-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amineHCID 767027172-(Pyridin-4-yl)cyclopropanecarbonyl chloride

生成物 1

HCID 67064769N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-(pyridin-4-yl)cyclopropanecarboxamide

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

In a round-bottomed flask was 2-(pyridin-4-yl)cyclopropanecarbonyl chloride (7D, 190 mg, 1.05 mmol) added in Pyridine (2 mL) to give a yellow suspension. 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 213 mg, 0.951 mmol) was added portionwise at 0° C. The temperature was slowly raised to room temperature. The reaction was quenched with saturated sodium bicarbonate and partitioned between ethyl acetate and water. The separated organic layer was dried over Mg2SO4, filtered, and concentrated under reduced pressure (3×100 mL). The reaction mixture was filtered and purified by preparatory, 5-95% (10 mM NH4HCO3 (aq)/10 mM NH4HCO3 in 20/80 (v/v) H2O/MeCN). Received 9 mg (3%) of yellow solid. 1H NMR (DMSO-d6) δ: 11.32 (s, 1H), 8.46 (d, J=6.1 Hz, 2H), 7.94-8.06 (m, 2H), 7.88 (s, 1H), 7.53-7.67 (m, 3H), 7.15-7.26 (m, 2H), 6.33 (s, 1H), 2.37 (s, 3H), 1.50-1.66 (m, 2H). ESI-MS: m/z 370.0 (M+H)+.

後処理

  1. customIn a round-bottomed flask was
  2. customto give a yellow suspension
  3. customThe reaction was quenched with saturated sodium bicarbonate
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe separated organic layer was dried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (3×100 mL)
  8. filtrationThe reaction mixture was filtered
  9. custompurified by preparatory, 5-95% (10 mM NH4HCO3 (aq)/10 mM NH4HCO3 in 20/80 (v/v) H2O/MeCN)

出典と根拠

ORDレコード
ord-e6a31b3f4b7d4d5c9eda3674d6373cf4
出典データセット
uspto-grants-2014_12
特許番号
US08921358B2

反応ノート

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