3-{1-[6-(3-bromo-7,8-dihydro-5H-1,6-naphthyridin-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one → 3-{1-[6-(7,8-dihydro-5H-1,6-naphthyridin-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 74644Notes

Reaction equation

HRID 74644 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][N:8]([C:12]([C:14]3[N:19]=[CH:18][N:17]=[C:16]([N:20]4[CH2:25][CH2:24][CH:23]([N:26]5[CH2:32][CH2:31][C:30]6[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:29]=6[NH:28][C:27]5=[O:39])[CH2:22][CH2:21]4)[CH:15]=3)=[O:13])[CH2:9][C:10]=2[CH:11]=1.[H][H]>[Pd].CO>[N:4]1[C:5]2[CH2:6][CH2:7][N:8]([C:12]([C:14]3[N:19]=[CH:18][N:17]=[C:16]([N:20]4[CH2:25][CH2:24][CH:23]([N:26]5[CH2:32][CH2:31][C:30]6[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:29]=6[NH:28][C:27]5=[O:39])[CH2:22][CH2:21]4)[CH:15]=3)=[O:13])[CH2:9][C:10]=2[CH:11]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 583866353-{1-[6-(3-bromo-7,8-dihydro-5H-1,6-naphthyridin-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 426134533-{1-[6-(7,8-dihydro-5H-1,6-naphthyridin-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a hydrogen atmosphere 77 mg (0.12 mmol) 3-{1-[6-(3-bromo-7,8-dihydro-5H-1,6-naphthyridin-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 40 mg palladium on charcoal (10%) were hydrogenated in 10 mL methanol at 50° C. under 50 psi hydrogen pressure. Then the catalyst was removed by suction filtering and the filtrate was evaporated down i. vac. The residue was purified by preparative HPLC. The product fractions were combined and lyophilised.

Workup

  1. customThen the catalyst was removed by suction
  2. filtrationfiltering
  3. customthe filtrate was evaporated down i
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a7ee3a2fda2a4339966f01710926ccbb
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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