3-{1-[6-(4-Amino-3-methyl-5-nitro-phenoxy)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one → 3-{1-[6-(3,4-Diamino-5-methyl-phenoxy)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

HRID 1846454Notes

Reaction equation

HRID 1846454 reaction equation
[NH2:1][C:2]1[C:34]([N+:35]([O-])=O)=[CH:33][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[CH2:25][CH2:24][C:23]5[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:22]=5[NH:21][C:20]4=[O:32])[CH2:15][CH2:14]3)[CH:8]=2)=[CH:4][C:3]=1[CH3:38]>CO.[Pd]>[NH2:35][C:34]1[CH:33]=[C:5]([CH:4]=[C:3]([CH3:38])[C:2]=1[NH2:1])[O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([N:13]2[CH2:14][CH2:15][CH:16]([N:19]3[CH2:25][CH2:24][C:23]4[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:22]=4[NH:21][C:20]3=[O:32])[CH2:17][CH2:18]2)[CH:8]=1

Participants

4

Reactant 1

HCID 669782863-{1-[6-(4-Amino-3-methyl-5-nitro-phenoxy)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one

Product 1

HCID 669783753-{1-[6-(3,4-Diamino-5-methyl-phenoxy)-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

830 mg (1.60 mmol) 3-{1-[6-(4-amino-3-methyl-5-nitro-phenoxy)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one in 20 mL MeOH were combined with 100 mg palladium on charcoal (Pd/C 10%) and hydrogenated for 8 h under a hydrogen atmosphere of 50 psi. After the catalyst had been removed by suction filtering, the filtrate was evaporated down and the residue was reacted further as the crude product.

Workup

  1. customAfter the catalyst had been removed by suction
  2. filtrationfiltering
  3. customthe filtrate was evaporated down
  4. customthe residue was reacted further as the crude product

Sources & evidence

ORD record
ord-5a88f4d80f294d96a095e5c13ebe3edf
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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