HCID 88293119, compound → HCID 18929586, compound

HRID 1599076Notes

Reaction equation

HRID 1599076 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:11])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[C:4](=[O:34])[C:3]1=[N:35]NC1C=CC=CC=1>[Zn].C(O)(=O)C>[NH2:35][CH:3]1[C:2](=[O:1])[N:8]([CH2:9][C:10]([N:12]([CH:21]([CH3:23])[CH3:22])[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[O:11])[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[C:4]1=[O:34]

Participants

4

Reactant 1

HCID 88293119HCID 88293119, compound

Product 1

HCID 18929586HCID 18929586, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-[2,4-Dioxo-3(phenyl-hydrazono)-5-pyrdin-2-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (460 mg), zinc dust (430 mg) and acetic acid (5.6 ml) was stirred at rt for 3 h. The solids were removed by filtration through celite, the filtrate was concentrated in vacuo and the residue azeotroped with hexane. The residue was dissolved in ethyl acetate (50 ml) and washed with 2N aqueous sodium bicarbonate (2×30 ml), water, (30 ml), brine (30 ml), dried (MgSO4) and concentrated in vacuo to afford the crude product (270 mg) which was used without further purification. 1H NMR (300 MHz, CDCl3); 1.03 (d, J=7 Hz, 6H), 3.79 (s, 3H), 4.02 (d J=10 Hz, 1H), 4.40 (s, 1H), 4.42 (d, J=10 Hz, 1H), 5.0 (sept, J=7.1 Hz, 1H), 6.8-7.3 (m, 10H), 7.44 (d, J=8.0 Hz 1H), 7.68 (d, J=8.0 Hz, 1H), 7.80 (m, 1H), 8.42 (d, J=3.9 Hz, 1H). Tlc (10% MeOH, CH2Cl2) Rf=0.23.

Workup

  1. customThe solids were removed by filtration through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue azeotroped with hexane
  4. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  5. washwashed with 2N aqueous sodium bicarbonate (2×30 ml), water, (30 ml), brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0dcdcc4a02e441ecb18e7064fffc7cfc
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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