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 1748667노트

반응식

HRID 1748667 반응식
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]

참가 물질

6

반응물 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

생성물 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-carboxamide수율 54.1%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 10340Sodium Carbonate용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b4bd4ea783a74cb895ac0723fb536f4f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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