Propanedioyl dichloride → HCID 10813725, compound

HRID 343173Notes

Reaction equation

HRID 343173 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][C:3](Cl)=[O:4].[CH:8]([N:11]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36])[C:12](=[O:28])[CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:10])[CH3:9]>C1COCC1>[O:6]=[C:1]1[N:14]([CH2:13][C:12]([N:11]([CH:8]([CH3:10])[CH3:9])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])=[O:28])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:3](=[O:4])[CH2:2]1

Participants

4

Reactant 2

HCID 74269Propanedioyl dichlorideHCID 10668079HCID 10668079, compound

Product 1

HCID 10813725HCID 10813725, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Malonyl dichloride (0.50 mL) in THF (22 mL) is added dropwise over 35 min to a 0° C. solution of N-Isopropyl-N-(2-methoxy-phenyl)-2-(2-phenylamino-phenylamino) acetamide, prepared as in Part C, (1.90 g, 4.87 mmol) in THF (45 mL) and the resultant mixture allowed to attain RT overnight. The solvents were removed in vacuo and the residue purified by silica gel flash column chromatography using 2% methanol in methylene chlorideas eluent to afford 2-(-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(2-methoxy-phenyl) acetamide (770 mg) as a cream foam, which exists as 3:2 mixture of rotamers (major rotamer recorded): 1H NMR (300 MHz, CDCl3) δ7.60-6.90 (m, 13H), 5.05 (m, 1H, J=6.9), 4.60-3.40 (m, 7H), 1.12 (m, 6H).

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-975f5c43bd2b43f5a63777fa8ca6d9f0
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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