Water → HCID 178517539, compound

HRID 1182855Notes

Reaction equation

HRID 1182855 reaction equation
FC(F)(F)C([N:5]1[CH2:10][CH2:9][CH:8]([C:11](Cl)=O)[CH2:7][CH2:6]1)=O.[Br:16][C:17]1[CH:18]=[CH:19][C:20]2[C:21]3[N:29]=C(N4CCNCC4)[N:27]=[C:26]([O:36]CC)[C:22]=3[NH:23][C:24]=2[CH:25]=1.O>C(Cl)Cl.N1C=CC=CC=1>[Br:16][C:17]1[CH:18]=[CH:19][C:20]2[C:21]3[N:29]=[C:11]([CH:8]4[CH2:7][CH2:6][NH:5][CH2:10][CH2:9]4)[N:27]=[C:26]([OH:36])[C:22]=3[NH:23][C:24]=2[CH:25]=1

Participants

6

Reactant 3

HCID 962WaterHCID 110859891-(Trifluoroacetyl)piperidine-4-carbonyl chlorideHCID 66863934HCID 66863934, compound

Product 1

HCID 178517539HCID 178517539, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

767 mg (3.15 mmol) 1-(2,2,2-trifluoroacetyl)piperidine-4-carboxylic acid chloride dissolved in CH2Cl2 was slowly added drop-wise to 526 mg (2.10 mmol) 3-amino-6-bromo-1H-indole-2-carboxylic acid amide (Example 4) in pyridine at 0° C. Then, stirring was carried out at room temperature for 40 min. After the addition of water, the solvent was removed in vacuo and the residue was taken up in methanol. After the addition of 2 M NaOH (excess), the reaction was kept at reflux for 45 min. Thereafter, the methanol was removed in vacuo, the precipitate was sucked off and washed with water. 652 mg (89%) 7-bromo-2-(4-piperidyl)-5H-pyrimido[5,4-b]indol-4-ol was obtained. ESI-MS [m/z]: 347, 349 [M+H]+

Workup

  1. customat 0° C
  2. customthe solvent was removed in vacuo
  3. additionAfter the addition of 2 M NaOH (excess)
  4. temperatureat reflux for 45 min
  5. customThereafter, the methanol was removed in vacuo
  6. washwashed with water

Sources & evidence

ORD record
ord-692580a61af345e7887356edf3f6c3ec
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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