2-Chloro-4-(trifluoromethyl)pyrimidine → HCID 67432560, compound

HRID 1887090Notes

Reaction equation

HRID 1887090 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[N:14][CH:13]=[CH:12]3)[CH2:4][CH2:3]1.[Cl:19][C:20]1[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=1>N1C=CC=CC=1.CN(C=O)C>[ClH:19].[F:27][C:26]([F:29])([F:28])[C:24]1[CH:23]=[CH:22][N:21]=[C:20]([N:2]2[CH2:7][CH2:6][CH:5]([O:8][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[CH:15]=[N:14][CH:13]=[CH:12]4)[CH2:4][CH2:3]2)[N:25]=1

Participants

5

Reactant 2

HCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 674289666-(Piperidin-4-yloxy)-isoquinoline hydrochloride

Product 1

HCID 67432560HCID 67432560, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

75 mg of 6-(Piperidine-4-yloxy)-isoquinoline-Hydrochloride (124) are dissolved in 5 mL of dry pyridine and 5 mL of DMF. 55 mg 2-Chlor-4-trifluoromethyl-pyrimidine are added and the solution is stirred at 60° C. for 3 hours. The solvents are removed in vacuo and the residue is taken up in brine and extracted three times with ethyl acetate. The combined organic layers are dried over magnesium sulfate, evaporated to dryness and the crude product is purified by preparative HPLC. The product is converted into the corresponding HCl salt by taking up the product in 20 mL of 1 N hydrochloric acid followed by lyophilization. Yield: 29 mg. Rt=1.69 min (Method #2). Detected mass: 375.1 (M+H+).

Workup

  1. customThe solvents are removed in vacuo
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. customevaporated to dryness
  5. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-57a249dbc8784933a0d327387aed7f08
Source dataset
uspto-grants-2013_08
Patent number
US08501736B2

Reaction notes

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