Dichloromethane → 3-[4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-6'-oxo-3,4,5,6.1'.6'-hexa-hydro-2H-[1,2']bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 469379Notes

Reaction equation

HRID 469379 reaction equation
C1COCC1.C(Cl)Cl.C([O:16][C:17]1[N:22]=[C:21]([N:23]2[CH2:28][CH2:27][CH:26]([N:29]3[CH2:35][CH2:34][C:33]4[CH:36]=[C:37]([O:40][CH3:41])[CH:38]=[CH:39][C:32]=4[NH:31][C:30]3=[O:42])[CH2:25][CH2:24]2)[CH:20]=[C:19]([C:43]([C:45]2[CH:55]=[C:54]([CH3:56])[C:48]3[N:49]([CH3:53])[C:50](=[O:52])[O:51][C:47]=3[CH:46]=2)=[O:44])[CH:18]=1)C1C=CC=CC=1>[Pd].CO>[CH3:53][N:49]1[C:48]2[C:54]([CH3:56])=[CH:55][C:45]([C:43]([C:19]3[CH:20]=[C:21]([N:23]4[CH2:28][CH2:27][CH:26]([N:29]5[CH2:35][CH2:34][C:33]6[CH:36]=[C:37]([O:40][CH3:41])[CH:38]=[CH:39][C:32]=6[NH:31][C:30]5=[O:42])[CH2:25][CH2:24]4)[NH:22][C:17](=[O:16])[CH:18]=3)=[O:44])=[CH:46][C:47]=2[O:51][C:50]1=[O:52]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 581811453-[6'-benzyloxy-4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetra-hydro-2H-[1,2']bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Product 1

HCID 252683853-[4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-6'-oxo-3,4,5,6.1'.6'-hexa-hydro-2H-[1,2']bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

30 mg palladium on charcoal (Pd/C 10%), 30 mL THF and 30 mL DCM were added to 0.13 g (0.20 mmol) 3-[6′-benzyloxy-4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one in 20 mL MeOH and the mixture was hydrogenated for 1.5 h under a hydrogen atmosphere. After filtration of the reaction mixture the solvent was evaporated down i. vac. The residue was purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. filtrationAfter filtration of the reaction mixture the solvent
  2. customwas evaporated down i
  3. customThe residue was purified by preparative HPLC-MS
  4. additionThe fractions containing the product
  5. customfreeze-dried

Sources & evidence

ORD record
ord-2b70aec477514673991b97ab4f01df1c
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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