4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)morpholine → N-{5-Cyano-6-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748667ノート

反応式

HRID 1748667 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=3)[C:15]=2[CH3:16])=[O:10])=[CH:4][C:3]=1[C:27]#[N:28].CC1(C)C(C)(C)OB([C:37]2[CH2:42][CH2:41][CH:40]([N:43]3[CH2:48][CH2:47][O:46][CH2:45][CH2:44]3)[CH2:39][CH:38]=2)O1>O1CCCC1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([C:3]1[CH:4]=[C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][N:18]=3)[C:15]=2[CH3:16])=[O:10])[CH:6]=[N:7][C:2]=1[C:37]1[CH2:42][CH2:41][CH:40]([N:43]2[CH2:44][CH2:45][O:46][CH2:47][CH2:48]2)[CH2:39][CH:38]=1)#[N:28]

参加物

6

反応物 2

HCID 592386904-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)morpholineHCID 86692611N-(6-chloro-5-cyanopyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

生成物 1

HCID 86692612N-{5-Cyano-6-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide収率 54.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 10340Sodium Carbonate溶媒

反応条件

温度
90 °C

実験手順

N-(6-Chloro-5-cyanopyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (200 mg), 4-[4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)cyclohex-3-en-1-yl]morpholine (159 mg) described in Reference Example 166 and tetrakis(triphenylphosphine)palladium (57 mg) were dissolved in a mixture of tetrahydrofuran (1 ml) and 1M aqueous solution of sodium carbonate (0.54 ml), and stirred at 90° C. After completion of the reaction, the reaction solution was left stand, filtered through Celite, washed with chloroform and the filtrate was concentrated. Water was added to the resulting residue and the precipitate was filtered. The obtained solid was refluxed in ethanol, the resulting solution was left stand, the precipitated solid was collected by filtration and dried in vacuo to give the titled compound (143 mg) as a pale yellow solid.

後処理

  1. customAfter completion of the reaction
  2. waitthe reaction solution was left stand
  3. filtrationfiltered through Celite
  4. washwashed with chloroform
  5. concentrationthe filtrate was concentrated
  6. additionWater was added to the resulting residue
  7. filtrationthe precipitate was filtered
  8. temperatureThe obtained solid was refluxed in ethanol
  9. waitthe resulting solution was left stand
  10. filtrationthe precipitated solid was collected by filtration
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-b4bd4ea783a74cb895ac0723fb536f4f
出典データセット
uspto-grants-2015_10
特許番号
US09150555B2

反応ノート

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