HCID 67696645, compound → HCID 67697134, compound

HRID 343133Notes

Reaction equation

HRID 343133 reaction equation
C([O:8][CH2:9][CH:10]1[C:16](=[O:17])[N:15]([CH2:18][C:19]([N:21]([CH:30]([CH3:32])[CH3:31])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[O:20])[C:14]2[CH:33]=[CH:34][CH:35]=[CH:36][C:13]=2[N:12]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:11]1=[O:43])C1C=CC=CC=1>[Cl-].[Na+].O.C(OCC)(=O)C.[Pd]>[OH:8][CH2:9][CH:10]1[C:16](=[O:17])[N:15]([CH2:18][C:19]([N:21]([CH:30]([CH3:32])[CH3:31])[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[O:20])[C:14]2[CH:33]=[CH:34][CH:35]=[CH:36][C:13]=2[N:12]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:11]1=[O:43]

Participants

4

Reactant 1

HCID 67696645HCID 67696645, compound

Product 1

HCID 67697134HCID 67697134, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 131718255Brine ethyl acetateSolvent

Procedure

To a stirring solution of 460 mg (0.80 mmol) of 2-[3-(Benzyloxymethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide in 10 mL of DMF/CHCl3 1/1 is added 200 mg of 10% Pd/C. The resulting mixture is stirred at RT over an atmosphere of H2 gas (balloon) for 6 h. The reaction mixture is filtered through a pad of Celite to remove the catalyst, rinsing with EtOAc. The filtrate is diluted further with 20 mL of EtOAc and extracted with H2O (2×40 mL). The organic layer is separated, dried (MgSO4), and the solvents removed in vacuo. Purification by trituration with EtOAc/Et2O 1/1 afforded 365 mg of the title compound as a white solid: mp 136°-139° C.; 1H NMR (CDCl3, 400 MHz) δ7.40-7.19 (m, 8H), 7.10 (m, 2H), 6.94 (m, 3H), 4.99 (m, 1H), 4.28 (m, 2H), 4.15 (m, 2H), 3.84 (s, 3H), 3.65 (t, 1H, J=6.9), 2.37 (t, 1H, J=7.3), 1.06 (2×d, 6H, J=6.3); low resolution MS (FAB)m/e 488 (MH+), 323, 277; Anal. (C28H29N3O5) Calcd. C, 68.98; H, 6.00; N, 8.62 Found C, 67.05; H, 5.99; N, 8.33.

Workup

  1. filtrationThe reaction mixture is filtered through a pad of Celite
  2. customto remove the catalyst
  3. washrinsing with EtOAc
  4. additionThe filtrate is diluted further with 20 mL of EtOAc
  5. extractionextracted with H2O (2×40 mL)
  6. customThe organic layer is separated
  7. dry with materialdried (MgSO4)
  8. customthe solvents removed in vacuo
  9. customPurification by trituration with EtOAc/Et2O 1/1

Sources & evidence

ORD record
ord-7e51cbc69a004b1fb0c52ac7326c200a
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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