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N-Isopropyl-2-[5-(4-methoxy-benzyl)-2,4-dioxo-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-(4-methoxy-phenyl)-acetamide → 2-[3-Amino-5-(4-methoxybenzyl)-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)-acetamide

HRID 1599088
Notes
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Reaction equation

HRID 1599088 reaction equation
[CH:1]([N:4]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)[C:5](=[O:37])[CH2:6][N:7]1[C:13](=[O:14])[C:12](=[N:15]NC2C=CC=CC=2)[C:11](=[O:23])[N:10]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:9]2[CH:33]=[CH:34][CH:35]=[CH:36][C:8]1=2)([CH3:3])[CH3:2]>C(O)(=O)C.[Zn]>[NH2:15][CH:12]1[C:13](=[O:14])[N:7]([CH2:6][C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[C:38]2[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)=[O:37])[C:8]2[CH:36]=[CH:35][CH:34]=[CH:33][C:9]=2[N:10]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)[C:11]1=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 86752412N-Isopropyl-2-[5-(4-methoxy-benzyl)-2,4-dioxo-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-(4-methoxy-phenyl)-acetamide

Product 1

HCID 189295902-[3-Amino-5-(4-methoxybenzyl)-2,4-dioxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(4-methoxyphenyl)-acetamideYield 73.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176
Acetic Acid
Solvent

Procedure

To a stirred solution of N-Isopropyl-2-[5-(4-methoxy-benzyl)-2,4-dioxo-3-(phenyl-hydrazono)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-(4-methoxy-phenyl)-acetamide (4.55 g, 7.51 mmol) in acetic acid (50 mL) was added zinc dust (4.50 g) and the resultant mixture was stirred 4 hours at ambient temperature. The zinc was separated by filtration, the filtrate was concentrated in vacuo, and the resultant oil partitioned between water (150 mL) and ethyl acetate (250 mL). The pH was adjusted to 8 with 6N sodium hydroxide and the phases separated. The aqueous phase was extracted with ethyl acetate (2×80 mL) and the organics combined, dried with magnesium sulfate, filtered and concentrated in vacuo to a brown oil. The crude product was purified via flash chromatography on silica gel (70 g) eluting successively with EtOAc/Hexanes (2:1, 500 mL) and methylene chloride/methanol (19:1, 500 mL). Appropriate fractions were combined and concentrated to give the title compound (2:85 g, 5.52 mmol) as a brown oil: 1H NMR (300 MHz, CDCl3): d 7.43 (d, J=7.3 Hz, 1H), 7.30-7.19 (m, 4H), 7.05-6.90 (m, 5H), 6.59 (d, J=8.8 Hz, 2H), 5.13 (d, J=15.1 Hz, 1H), 5.00 (m, 1H), 4.86 (d, J=15.1 Hz, 1H), 4.25 (s, 1H), 4.21 (d, J=16.6 Hz, 1H), 3.85 (s, 3H), 3.69 (s, 3H), 3.48 (d, J=16.6 Hz, 1H), 1.09 (m, 6H); TLC (CH2 Cl2 /CH3OH (29:1)): Rf =0.11.

Workup

  1. customThe zinc was separated by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe resultant oil partitioned between water (150 mL) and ethyl acetate (250 mL)
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted with ethyl acetate (2×80 mL)
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to a brown oil
  9. customThe crude product was purified via flash chromatography on silica gel (70 g)
  10. washeluting successively with EtOAc/Hexanes (2:1, 500 mL) and methylene chloride/methanol (19:1, 500 mL)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-392d404bf45b46b78cb99fabe610ef0d
Source dataset
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05739129

Reaction notes

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