3-{1-[6-(4-Benzyloxy-3,5-dimethyl-benzoyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one → 3-{1-[6-(4-Hydroxy-3,5-dimethyl-benzoyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 469417Notes

Reaction equation

HRID 469417 reaction equation
C([O:8][C:9]1[C:42]([CH3:43])=[CH:41][C:12]([C:13]([C:15]2[N:20]=[CH:19][N:18]=[C:17]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:33][CH2:32][C:31]5[CH:34]=[C:35]([O:38][CH3:39])[CH:36]=[CH:37][C:30]=5[NH:29][C:28]4=[O:40])[CH2:23][CH2:22]3)[CH:16]=2)=[O:14])=[CH:11][C:10]=1[CH3:44])C1C=CC=CC=1.[H][H]>[Pd].CO>[OH:8][C:9]1[C:42]([CH3:43])=[CH:41][C:12]([C:13]([C:15]2[N:20]=[CH:19][N:18]=[C:17]([N:21]3[CH2:22][CH2:23][CH:24]([N:27]4[CH2:33][CH2:32][C:31]5[CH:34]=[C:35]([O:38][CH3:39])[CH:36]=[CH:37][C:30]=5[NH:29][C:28]4=[O:40])[CH2:25][CH2:26]3)[CH:16]=2)=[O:14])=[CH:11][C:10]=1[CH3:44]

Participants

5

Reactant 2

HCID 581811283-{1-[6-(4-Benzyloxy-3,5-dimethyl-benzoyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 581811093-{1-[6-(4-Hydroxy-3,5-dimethyl-benzoyl)-pyrimidin-4-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

70 mg (0.10 mmol) 3-{1-[6-(4-benzyloxy-3,5-dimethyl-benzoyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one and 20 mg palladium on charcoal (Pd/C 10%) in 10 mL MeOH were hydrogenated for 30 min at RT in a hydrogen atmosphere of 10 psi. After filtration of the reaction mixture the solvent was eliminated i. vac. and 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. customand the residue was purified by preparative HPLC-MS
  3. additionThe fractions containing the product
  4. customfreeze-dried

Sources & evidence

ORD record
ord-10e91efbf6d64abda2b86c8b3b4c99c1
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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