Diethyl Ether → HCID 178518691, compound

HRID 574005Notes

Reaction equation

HRID 574005 reaction equation
[F:1][C:2]1[C:3]([NH:16][C@@H:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)=[N:4][C:5]([NH:8][C:9]2[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.Br[C:24]1[NH:28][CH:27]=[N:26][N:25]=1.C(OCC)C>CO>[N:25]1[N:26]=[C:27]([N:19]2[CH2:20][CH2:21][CH2:22][C@@H:17]([NH:16][C:3]3[C:2]([F:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]4[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=4)[N:4]=3)[CH2:18]2)[NH:28][CH:24]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 71245036HCID 71245036, compoundHCID 178419482HCID 178419482, compound

Product 1

HCID 178518691HCID 178518691, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (R)-3-(5-fluoro-4-(piperidin-3-ylamino)pyrimidin-2-ylamino)pyridin-2(1H)-one (Preparation 22c, 50 mg, 0.16 mmol) and 3-bromo-4H-1,2,4-triazole (prepared as described in J. Med. Chem. 2004, 47(19), 4645, 12.2 mg, 0.08 mmol) was stirred and heated overnight at 150° C. The reaction mixture was cooled to ambient temperature and diluted with methanol. Diethyl ether was then added and the precipitate that formed was filtered. The filtrate was concentrated under reduced pressure and the resulting semisolid was suspended in diethyl ether and filtered to yield the title compound (12 mg, 40%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthe precipitate that formed
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e1f861fd030442b79ff47bfa383b22fe
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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