N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-3-(trifluoromethyl)-benzamide → HCID 178478733, compound

HRID 1244968Notes

Reaction equation

HRID 1244968 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:31])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)[N:3]=1.[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([NH2:39])[CH2:35][CH2:34]1>>[ClH:1].[ClH:1].[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([NH:39][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:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=3)[N:3]=2)[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 21922944N-[2-[(2-chloro-9-cyclopentyl-9H-purin-6-yl)-amino]-ethyl]-3-(trifluoromethyl)-benzamideHCID 178511674HCID 178511674, compound

Product 1

HCID 178478733HCID 178478733, compound

Conditions

Temperature
140 °C

Procedure

290 mg of the product obtained in Stage 1 above and 365 mg of trans-1,4-diaminocyclohexane are mixed together and the reaction medium is heated to approximately 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 206 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 206 mg of expected product
  6. customis recovered

Sources & evidence

ORD record
ord-36bbac99e9dc4333b1c1bfb2800bc79a
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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