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 2174957Notes

Reaction equation

HRID 2174957 reaction equation
[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]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 56947515Panulisib

Product 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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 109236242-Propylpentanoyl 2-propylpentanoateSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-d6e73ebda33042709195d40f67f49998
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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