Potassium Acetate → N-(5-(2-(cyanoimino)-1-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl)-3-(trifluoromethyl)pyridin-2-yl)-2-propylpentanamide

HRID 2174957노트

반응식

HRID 2174957 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[N:14]=[CH:13][C:12]4[N:18]([CH3:35])[C:19](=[N:32][C:33]#[N:34])[N:20]([C:21]5[CH:22]=[N:23][C:24]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:25][CH:26]=5)[C:11]=4[C:10]=3[CH:9]=2)=[CH:4][C:3]=1[C:36]([F:39])([F:38])[F:37].[C:40]([O-:43])(=O)[CH3:41].[K+]>C(OC(=O)C(CCC)CCC)(=O)C(CCC)CCC.O>[C:33]([N:32]=[C:19]1[N:18]([CH3:35])[C:12]2[CH:13]=[N:14][C:15]3[CH:16]=[CH:17][C:8]([C:5]4[CH:4]=[C:3]([C:36]([F:38])([F:37])[F:39])[C:2]([NH:1][C:40](=[O:43])[CH:41]([CH2:6][CH2:5][CH3:8])[CH2:2][CH2:3][CH3:4])=[N:7][CH:6]=4)=[CH:9][C:10]=3[C:11]=2[N:20]1[C:21]1[CH:22]=[N:23][C:24]([C:27]([C:30]#[N:31])([CH3:28])[CH3:29])=[CH:25][CH:26]=1)#[N:34]

참가 물질

5

반응물 2

HCID 517044Potassium AcetateHCID 56947515Panulisib

생성물 1

HCID 56599242N-(5-(2-(cyanoimino)-1-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl)-3-(trifluoromethyl)pyridin-2-yl)-2-propylpentanamide

시약·촉매·용매 2

HCID 962Water용매HCID 109236242-Propylpentanoyl 2-propylpentanoate용매

실험 절차

N-(8-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-1-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide (Example 5, 0.379 mmol) was stirred in valproic anhydride (5 mL). Potassium acetate (0.379 mmol) was added to it and the reaction was carried out at 110-115° C. for 2 h. The reaction mixture was cooled, diluted with water and extracted with ethyl acetate. Organic layer was concentrated, dried using anhydrous sodium sulfate and purified on silica gel column to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 10.21 (s, 1H), 9.32 (s, 1H), 9.08 (s, 1H), 8.63 (s, 1H), 8.44 (d, J=5.1 Hz, 1H), 8.28 (d, J=5.1 Hz, 1H), 8.18-8.15 (m, 1H), 8.01 (d, J=5.1 Hz, 1H), 7.06 (s, 1H), 3.94 (s, 3H), 1.77 (s, 3H), 1.56 (m, 2H), 1.35 (s, 6H), 1.23 (s, 1H), 0.91 (s, 6H); MS (m/z): 654.4 (M+1)+.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. concentrationOrganic layer was concentrated
  4. customdried
  5. custompurified on silica gel column

출처 및 근거

ORD 기록
ord-d6e73ebda33042709195d40f67f49998
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062046B2

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