1h-imidazole-1-carboxamide → 9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-N-{2-[(([2-(1-piperidinyl)ethyl]amino}carbonyl)amino]ethyl}-9H-purine-2-carboxamide

HRID 353612Notes

Reaction equation

HRID 353612 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][OH:24])[O:17]2)=[C:9]([NH:25][CH2:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:8]=1)=[O:6].[N:40]1([C:45](N)=[O:46])[CH:44]=[CH:43][N:42]=[CH:41]1>C1(C)C=CC=CC=1.C(O)(C)C>[OH:21][C@@H:20]1[C@H:19]([OH:22])[C@@H:18]([CH2:23][OH:24])[O:17][C@H:16]1[N:13]1[CH:12]=[N:11][C:10]2[C:14]1=[N:15][C:7]([C:5]([NH:4][CH2:3][CH2:2][NH:1][C:45]([NH:40][CH2:44][CH2:43][N:42]1[CH2:20][CH2:19][CH2:18][CH2:23][CH2:41]1)=[O:46])=[O:6])=[N:8][C:9]=2[NH:25][CH2:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 2653011h-imidazole-1-carboxamideHCID 60091691N-(2-Aminoethyl)-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxamide

Product 1

HCID 468865929-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-N-{2-[(([2-(1-piperidinyl)ethyl]amino}carbonyl)amino]ethyl}-9H-purine-2-carboxamideYield 145.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

N-(2-Aminoethyl)-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxamide (Preparation 17) (90 mg, 0.17 mmol) and N-[2-1-piperidinyl)ethyl]-1H-imidazole-1-carboxamide (Preparation 18) (40 mg, 0.18 mmol) were dissolved in a mixture of toluene (4 ml) and isopropanol (1 ml) and the solution heated under reflux for four hours. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with dichloromethane:methanol:concentrated aqueous ammonia (85:15:1.5, by volume). Product containing fractions were evaporated and the resulting solid triturated with diethyl ether, filtered and dried to afford the title compound as a white powder (85 mg).

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for four hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with dichloromethane
  5. additionProduct containing fractions
  6. customwere evaporated
  7. customthe resulting solid triturated with diethyl ether
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-2c0890ad28c74070b69cd26ecc8bfb89
Source dataset
uspto-grants-2004_06
Patent number
US06753322B2

Reaction notes

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