3-{1-[6-Chloro-5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyridazin-3-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one → 3-(1-{5-[Hydroxy-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-yl)-methyl]-pyridazin-3-yl}-piperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 469331Notes

Reaction equation

HRID 469331 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:20][CH2:19][C:18]4[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:17]=4[NH:16][C:15]3=[O:27])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[C:28]([C:30]1[CH:39]=[C:38]([CH3:40])[C:33]2[NH:34][C:35](=[O:37])[O:36][C:32]=2[CH:31]=1)=[O:29].[H][H]>[Pd].CO>[OH:29][CH:28]([C:30]1[CH:39]=[C:38]([CH3:40])[C:33]2[NH:34][C:35](=[O:37])[O:36][C:32]=2[CH:31]=1)[C:3]1[CH:4]=[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:20][CH2:19][C:18]4[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:17]=4[NH:16][C:15]3=[O:27])[CH2:10][CH2:9]2)[N:6]=[N:7][CH:2]=1

Participants

5

Reactant 2

HCID 252694613-{1-[6-Chloro-5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyridazin-3-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 581810963-(1-{5-[Hydroxy-(4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-yl)-methyl]-pyridazin-3-yl}-piperidin-4-yl)-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.25 g (0.40 mmol) 3-{1-[6-chloro-5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-pyridazin-3-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one, 0.10 mL (0.71 mmol) TEA and 50 mg palladium on charcoal (Pd/C 10%) in MeOH was hydrogenated for 3 h at 50° C. in a hydrogen atmosphere of 50 psi. After filtration of the reaction mixture the filtrate was evaporated down to approx. 3 mL and mixed with a little ice water. The precipitate formed was suction filtered and dried. The residue contained the desired product in the mixture and was used in the next step without further purification.

Workup

  1. filtrationAfter filtration of the reaction mixture the filtrate
  2. customwas evaporated down to approx. 3 mL
  3. additionmixed with a little ice water
  4. customThe precipitate formed
  5. filtrationfiltered
  6. customdried
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-d4487871667740ea92da1420049d6063
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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