N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide → N-({6-{[2,2-Bis(4-chlorophenyl)ethyl]amino}-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-9H-purin-2-yl}methyl)-N'-[2-(diisopropylamino)ethyl]urea

HRID 1293016Notes

Reaction equation

HRID 1293016 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][OH:20])[O:13]2)=[C:5]([NH:21][CH2:22][CH:23]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[N:4]=1.[CH:38]([N:41]([CH:52]([CH3:54])[CH3:53])[CH2:42][CH2:43][NH:44][C:45](N1C=CN=C1)=[O:46])([CH3:40])[CH3:39]>C(O)(C)C>[NH3:1].[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([CH:23]([C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[CH2:22][NH:21][C:5]2[N:4]=[C:3]([CH2:2][NH:1][C:45]([NH:44][CH2:43][CH2:42][N:41]([CH:52]([CH3:54])[CH3:53])[CH:38]([CH3:39])[CH3:40])=[O:46])[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][OH:20])[O:13]2)=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 21978296N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide2×HCID 60018575(2R,3R,4S,5R)-2-(2-(Aminomethyl)-6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol

Product 2

HCID 222AmmoniaHCID 10212303N-({6-{[2,2-Bis(4-chlorophenyl)ethyl]amino}-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-9H-purin-2-yl}methyl)-N'-[2-(diisopropylamino)ethyl]ureaYield 139.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(2R,3R,4S,5R)-2-(2-(Aminomethyl)-6-{[2,2-bis(4-chlorophenyl)ethyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol (0.1 g, 0.18 mmol) (Preparation 63) was dissolved in a mixture of isopropanol (0.5 ml) and Genklene (Trade Mark) (5 ml). N-[2-(Diisopropylamino)ethyl]-1H-imidazole-1-carboxamide (48 mg, 0.20 mmol) (Preparation 27) was added and the reaction mixture was heated under reflux for 2 hours. More N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide (35 mg, 0.15 mmol) (Preparation 27) was then added and the reaction mixture was heated under reflux for a further 2 hours. The reaction mixture was then allowed to cool and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:2 by volume) to give the title compound (0.09 g) as a gum.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for a further 2 hours
  5. temperatureto cool
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane
  8. temperaturemethanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane

Sources & evidence

ORD record
ord-9cffed3b509446b3be1527773c7c7c97
Source dataset
uspto-grants-2007_07
Patent number
US07238676B2

Reaction notes

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