Diisopropylethylamine → HCID 178495710, compound

HRID 2268381Notes

Reaction equation

HRID 2268381 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH2:4][CH2:3]1.CS(O[CH2:18][C:19]1[N:27]=[C:26]2[C:22]([N:23]=[CH:24][N:25]2[C@H:28]2[C@H:32]([OH:33])[C@H:31]([OH:34])[C@@H:30]([CH2:35][O:36][CH3:37])[O:29]2)=[C:21]([NH:38][CH2:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:20]=1)(=O)=O.C(N(C(C)C)C(C)C)C>C(O)C.ClCCl>[OH:33][C@@H:32]1[C@H:31]([OH:34])[C@@H:30]([CH2:35][O:36][CH3:37])[O:29][C@H:28]1[N:25]1[CH:24]=[N:23][C:22]2[C:26]1=[N:27][C:19]([CH2:18][NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH2:4][CH2:3]1)=[N:20][C:21]=2[NH:38][CH2:39][CH:40]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 59975278{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonateHCID 178505155HCID 178505155, compound

Product 1

HCID 178495710HCID 178495710, compoundYield 18.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-(trans-4-Aminocyclohexyl)methanesulfonamide (183 mg, 0.8 mmol) (preparation 33) was added to a stirred solution of {9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (230 mg, 0.4 mmol) (preparation 25) and N-ethyl-N-isopropyl-2-propanamine (210 mg, 1.6 mmol) in ethanol (3 ml) and dichloromethane (12 ml). The reaction mixture was stirred for 48 hr at room temperature. The solvent was then removed under reduced pressure and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed with brine and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (98:2:0.3) increasing in polarity to (90:10:1) to give the title compound (50 mg) as a foam. MS: 667 (MH+).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe ethyl acetate layer was separated
  4. washwashed with brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give a residue which
  8. customwas purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (98:2:0.3)
  9. temperatureincreasing in polarity to (90:10:1)

Sources & evidence

ORD record
ord-17a04cf5a57a4e88bd54f2e8079faa93
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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