Propanedioyl dichloride → HCID 69427209, compound

HRID 1375350Notes

Reaction equation

HRID 1375350 reaction equation
[O:1]=[C:2]([N:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:3][NH:4][C:5]1[C:6]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=1.[C:29](Cl)(=[O:34])[CH2:30][C:31](Cl)=[O:32]>C1COCC1>[O:1]=[C:2]([N:18]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:3][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:31](=[O:32])[CH2:30][C:29]1=[O:34]

Participants

4

Reactant 2

HCID 74269Propanedioyl dichlorideHCID 86602388HCID 86602388, compound

Product 1

HCID 69427209HCID 69427209, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To 100 mL of THF at 0° C. was added dropwise over 20 min simultaneously a solution of 8.0 g of the N1-[2-oxo-2-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)ethyl]-N2-phenylbenzene-1,2-diamine (8.0 g, 21.5 mM) in 100 mL of THF and solution of malonyl dichloride (2.40 mL, 25.8 mM) in 100 mL of THF. The resulting solution was stirred at RT for 20 h and the solvent removed in vacuo. The resultant material was purified by silica gel flash column chromatography using hexanes/EtOAc 1/1 and the combined filtrates evaporated in vacuo to give 7.5 g of product.

Workup

  1. customthe solvent removed in vacuo
  2. customThe resultant material was purified by silica gel flash column chromatography
  3. customthe combined filtrates evaporated in vacuo

Sources & evidence

ORD record
ord-a59e2d38ec02488598b390d1f9819191
Source dataset
uspto-grants-2007_01
Patent number
US07169773B2

Reaction notes

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