N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]ethyl]-4-fluoro-benzamide → HCID 178478738, compound

HRID 1244966Notes

Reaction equation

HRID 1244966 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:28])[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[N:3]=1.[NH2:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([NH2:36])[CH2:32][CH2:31]1>>[ClH:1].[ClH:1].[NH2:29][C@H:30]1[CH2:35][CH2:34][C@H:33]([NH:36][C:2]2[N:10]=[C:9]3[C:5]([N:6]=[CH:7][N:8]3[CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:4]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:28])[C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[N:3]=2)[CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 21922952N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]ethyl]-4-fluoro-benzamideHCID 178511674HCID 178511674, compound

Product 1

HCID 178478738HCID 178478738, compound

Conditions

Temperature
140 °C

Procedure

247 mg of the product obtained in Stage 1 above and 350 mg of trans-1,4-diaminocyclohexane are mixed together and the reaction medium is heated to 140° C. for 6 hours. After evaporating the solvent, chromatography on silica is carried out (eluent methylene chloride/methanol/ammonium hydroxide 85/15/1.5) followed by taking up in an ethanolic solution of hydrochloric acid, leaving to crystallize, separating, drying under reduced pressure and 130 mg of expected product is recovered.

Workup

  1. customAfter evaporating the solvent, chromatography on silica
  2. customleaving
  3. customto crystallize
  4. customseparating
  5. dry with materialdrying under reduced pressure and 130 mg of expected product
  6. customis recovered

Sources & evidence

ORD record
ord-f7f6014b7c474f92a4e076705b0c53c0
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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