1,4-Cyclohexadiene → HCID 51038624, compound

HRID 2039551Notes

Reaction equation

HRID 2039551 reaction equation
C([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][C:14]2[N:23]3[N:24]=[C:25]([NH2:27])[N:26]=[C:22]3[C:21]3[CH:20]=[CH:19][C:18]([F:28])=[CH:17][C:16]=3[N:15]=2)=[CH:11][C:10]=1[O:31][CH3:32])C1C=CC=CC=1.C1CC=CCC=1>CO.[Pd]>[NH2:27][C:25]1[N:26]=[C:22]2[N:23]([C:14]([CH2:13][C:12]3[CH:29]=[CH:30][C:9]([OH:8])=[C:10]([O:31][CH3:32])[CH:11]=3)=[N:15][C:16]3[CH:17]=[C:18]([F:28])[CH:19]=[CH:20][C:21]=32)[N:24]=1

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 51038409HCID 51038409, compound

Product 1

HCID 51038624HCID 51038624, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-(4-benzyloxy-3-methoxy-benzyl)-8-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-2-ylamine (0.04 g, 0.09 mmol) in MeOH (5 mL), prepared as described in example 34, were added 1,4-cyclohexadiene (0.1 mL, 1.40 mmol) and 10% Pd/C (0.02 g, 50% w/w). The reaction was heated at 70° C. for 1 h, then filtered through Celite® washing with MeOH and THF and evaporated, to afford the title compound (0.03 g, 97% yield).

Workup

  1. filtrationfiltered through Celite®
  2. washwashing with MeOH and THF
  3. customevaporated

Sources & evidence

ORD record
ord-77e6b48727e34858b7bab5e0a97ba5a4
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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