HCID 178487815, compound → HCID 178487813, compound

HRID 2273222Notes

Reaction equation

HRID 2273222 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH:17]2[NH:30][C:29]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH3:32])[N:27]=4)[N:22]=[CH:21][C:20]=3[O:19][CH2:18]2)[CH2:13][CH2:12]1)C1C=CC=CC=1>[Pd].CO.O1CCCC1>[CH3:32][O:31][C:26]1[N:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[N:22]=[CH:21][C:20]1[O:19][CH2:18][CH:17]([C@H:14]3[CH2:15][CH2:16][C@H:11]([NH2:10])[CH2:12][CH2:13]3)[NH:30][C:29]2=1

Participants

5

Reactant 1

HCID 178487815HCID 178487815, compound

Product 1

HCID 178487813HCID 178487813, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

10% Palladium on activated carbon (285 mg, 2.68 mmol, 1.0 eq) is added at room temperature to a stirred solution of [trans-4-(6-methoxy-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-cyclohexyl]-carbamic acid benzyl ester (1.20 g, 2.68 mmol, 1.0 eq) in methanol (80 mL) and tetrahydrofuran (8 mL). The resulting mixture is stirred under hydrogen flow (1 bar) at 40° C. for 16 hours. The catalyst is then removed by filtration and the solution is concentrated to afford trans-4-(6-methoxy-3,4-dihydro-2H-1-oxa-4,5,9-triaza-phenanthren-3-yl)-cyclohexylamine as a yellow solid (620 mg, 74% yield) which is directly engaged in the next step.

Workup

  1. customThe catalyst is then removed by filtration
  2. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-ff134f7d31e344f0831531eb0fc9cecb
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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