Phthalimide → HCID 22142379, compound

HRID 2297228Notes

Reaction equation

HRID 2297228 reaction equation
ClC1C=C(Cl)C=CC=1C(=O)CCl.[C:13]1(=O)[NH:17][C:16](=O)[C:15]2=CC=CC=C12.C1(=O)OC(=O)CC1O.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.[NH2:38][C:39]1[N:44]=[C:43]([NH:45][CH2:46][CH2:47][NH:48][C:49]2[N:54]=[C:53]([C:55]3[CH:60]=[CH:59][C:58]([Cl:61])=[CH:57][C:56]=3[Cl:62])[C:52]([N:63]3[C:67](=[O:68])[CH:66]=CC3=O)=[CH:51][N:50]=2)[CH:42]=[CH:41][C:40]=1[N+:70]([O-:72])=[O:71]>>[NH2:38][C:39]1[N:44]=[C:43]([NH:45][CH2:46][CH2:47][NH:48][C:49]2[N:54]=[C:53]([C:55]3[CH:60]=[CH:59][C:58]([Cl:61])=[CH:57][C:56]=3[Cl:62])[C:52]([N:63]3[C:67](=[O:68])[CH2:66][CH:37]([N:32]4[CH2:15][CH2:16][N:17]([CH3:13])[CH2:34][CH2:33]4)[C:36]3=[O:35])=[CH:51][N:50]=2)[CH:42]=[CH:41][C:40]=1[N+:70]([O-:72])=[O:71]

Participants

6

Reactant 5

HCID 6809PhthalimideHCID 8083MorpholineHCID 202502,2',4'-TrichloroacetophenoneHCID 11571795HCID 11571795, compoundHCID 221430891-[2-({2-[(6-Amino-5-nitro(2-pyridyl))amino]ethyl}amino)-4-(2,4-dichlorophenyl)pyrimidin-5-yl]-3-pyrroline-2,5-dione

Product 1

HCID 22142379HCID 22142379, compound

Procedure

1-[2-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-4-(2,4-dichlorophenyl-pyrimidin-5-yl]-3-(4-methylpiperazinyl)pyrrolidine-2,5-dione was made in accordance with the foregoing procedures through steps A using 1-(2,4-dichlorophenyl)-2-chloroethan-1-one and phthalimide, B, C using amino{2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}-carboxamidine, D, E, K using malic anhydride, and F. Large excess of morpholine was added to clean fractions of 1-[2-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-4-(2,4-dichlorophenyl)pyrimidin-5-yl]-3-pyrroline-2,5-dione concentrated in vacuo, and purified by column chromatography eluting with 5-10% methanol/methylene chloride.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by column chromatography
  3. washeluting with 5-10% methanol/methylene chloride

Sources & evidence

ORD record
ord-e2a26f9aaf2f4a429b8e962bc7ee5cb0
Source dataset
uspto-grants-2002_12
Patent number
US06489344B1

Reaction notes

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