Propanedioyl dichloride → HCID 10719633, compound

HRID 343147Notes

Reaction equation

HRID 343147 reaction equation
[CH:1]1([N:6]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:7](=[O:23])[CH2:8][NH:9][CH:10]2[CH:15]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:13][CH:12]=[CH:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:32](Cl)(=[O:37])[CH2:33][C:34](Cl)=[O:35]>C1COCC1>[CH:1]1([N:6]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[C:7](=[O:23])[CH2:8][N:9]2[C:34](=[O:35])[CH2:33][C:32](=[O:37])[N:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 74269Propanedioyl dichlorideHCID 54236405HCID 54236405, compound

Product 1

HCID 10719633HCID 10719633, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 419 mg (1.01 mmol) N-Cyclopentyl-N-(4-methoxy-phenyl)-2-(6-phenylamino-cyclohexa-2,4-dienylamino)-acetamide, prepared as in Part B, in 5 mL THF is added 170 mg (1.21 mmol, 1.2 equiv) Malonyl dichloride dissolved in 2 mL THF dropwise at 0° C. The reaction is stirred 1 h at 0° C. followed by 18 h at ambient temperature. The solvent is removed in vacuo and the residue purified by flash chromatography on 15 g silica gel eluted with EtOAc/Hexanes (1:1, 300 mL). Appropriate fractions were combined and concentrated in vacuo to give 249 mg (0.515 mmol) of N-Cyclopentyl-2-(2,4-dioxo-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-(4-methoxy-phenyl)-acetamide as a clear glass: 1H NMR (CDCl3, 300 MHz) δ7.43-7.20 (m, 8H), 7.09 (m, 2H), 6.97 (m, 3H), 4.95 (m, 1H), 4.38 (d, 1H, J=16.4), 4.06 (d, 1H, J=16.3), 3.84 (s, 3H), 3.59 (d, 1H, J=12.0), 3.49 (d, 1H, J=11.9), 1.90 (m, 2H), 1.52 (m, 4H), 1.35 (m, 2H); TLC Rf =0.16 (EtOAc/Hexanes, 1:1).

Workup

  1. waitfollowed by 18 h at ambient temperature
  2. customThe solvent is removed in vacuo
  3. customthe residue purified by flash chromatography on 15 g silica gel
  4. washeluted with EtOAc/Hexanes (1:1, 300 mL)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-374953ad713e4e7d900c9429e424d260
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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