HCID 10417675, compound → HCID 57848519, compound

HRID 736941Notes

Reaction equation

HRID 736941 reaction equation
[NH2:1][C:2]1[C:45]([C:46]([F:49])([F:48])[F:47])=[CH:44][C:5]([CH2:6][C@@H:7]([CH2:23][C:24]([N:26]2[CH2:31][CH2:30][CH:29]([N:32]3[CH2:38][CH2:37][C:36]4[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=4[NH:34][C:33]3=[O:43])[CH2:28][CH2:27]2)=[O:25])[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1Br>CO.[Pd]>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]([CH2:23][C:24]([N:26]2[CH2:27][CH2:28][CH:29]([N:32]3[CH2:38][CH2:37][C:36]4[CH:39]=[CH:40][CH:41]=[CH:42][C:35]=4[NH:34][C:33]3=[O:43])[CH2:30][CH2:31]2)=[O:25])[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]3)[CH2:12][CH2:11]2)=[O:9])=[CH:44][C:45]=1[C:46]([F:49])([F:48])[F:47]

Participants

4

Reactant 1

HCID 10417675HCID 10417675, compound

Product 1

HCID 57848519HCID 57848519, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

100 mg 10% Pd/C were added to a solution of 150 mg (0.2 mmol) (S)-2-(4-amino-3-bromo-5-trifluoromethyl-benzyl)-1-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butan-1,4-dione in 20 mL MeOH and the reaction mixture was hydrogenated at 50 psi H2 for 3 h at RT. The catalyst was suction filtered, the solvent was evaporated down i.vac., the residue was combined with 5% K2CO3 solution and EtOAc, the organic phase was separated off and evaporated down i.vac. The residue was triturated with diisopropylether and suction filtered.

Workup

  1. filtrationfiltered
  2. customthe solvent was evaporated down i.vac
  3. customthe organic phase was separated off
  4. customevaporated down i.vac
  5. customThe residue was triturated with diisopropylether and suction
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5f5acc42f407473dacf1bab9a171293a
Source dataset
uspto-grants-2009_09
Patent number
US07595312B2

Reaction notes

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