HCID 11520351, compound → HCID 11549165, compound

HRID 642819Notes

Reaction equation

HRID 642819 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:34][C:35]3[CH:40]=[C:39]([N+:41]([O-])=O)[C:38]([NH2:44])=[C:37]([CH3:45])[CH:36]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:46]=[CH:47][CH:48]=[CH:49][C:4]=2[NH:3]1.[H][H]>C1COCC1.[Pd]>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:34][C:35]3[CH:36]=[C:37]([CH3:45])[C:38]([NH2:44])=[C:39]([NH2:41])[CH:40]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:46]=[CH:47][CH:48]=[CH:49][C:4]=2[NH:3]1

Participants

5

Reactant 2

HCID 11520351HCID 11520351, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11549165HCID 11549165, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

260 mg (0.37 mmol) (R)-1-(4-amino-3-methyl-5-nitro-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate were dissolved in 25 mL THF and combined with 130 mg 10% Pd/C. The mixture was hydrogenated for 4.5 h in a Parr apparatus at 50° C. under 50 psi hydrogen pressure. Then the catalyst was filtered off, the filtrate was evaporated down i.vac., the residue was dissolved in a little DCM, combined with diethyl ether, the precipitate was suction filtered and dried.

Workup

  1. filtrationThen the catalyst was filtered off
  2. customthe filtrate was evaporated down i.vac
  3. dissolution, the residue was dissolved in a little DCM
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-4026d6efaef148f78c42e653a362cc6c
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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