Diisopropylethylamine → 2-[({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)amino]-N,N-diisopropylacetamide

HRID 2268372

Reaction equation

HRID 2268372 reaction equation
CS(O[CH2:6][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][O:24][CH3:25])[O:17]2)=[C:9]([NH:26][CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:8]=1)(=O)=O.[NH2:41][CH2:42][C:43]([N:45]([CH:49]([CH3:51])[CH3:50])[CH:46]([CH3:48])[CH3:47])=[O:44].C(N(C(C)C)C(C)C)C>>[OH:21][C@@H:20]1[C@H:19]([OH:22])[C@@H:18]([CH2:23][O:24][CH3:25])[O:17][C@H:16]1[N:13]1[CH:12]=[N:11][C:10]2[C:14]1=[N:15][C:7]([CH2:6][NH:41][CH2:42][C:43]([N:45]([CH:46]([CH3:48])[CH3:47])[CH:49]([CH3:50])[CH3:51])=[O:44])=[N:8][C:9]=2[NH:26][CH2:27][CH:28]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 183484282-amino-N,N-bis(propan-2-yl)acetamideHCID 59975278{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

Product 1

HCID 599753112-[({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)amino]-N,N-diisopropylacetamideYield 11.3%

Procedure

The title compound was prepared by a similar method to example 40 using {9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (preparation 25) (374 mg, 0.66 mmol), 2-amino-N,N-diisopropylacetamide (520 mg, 3.3 mmol) (preparation 22) and N-ethyl-N-isopropyl-2-propanamine (170 mg, 1.32 mmol). The compound was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (95:5:0.5) increasing in polarity to (90:10:1). The solvent was removed under reduced pressure to give a residue which was triturated with diethyl ether to give the title compound (47 mg) as a solid. MS: 632 (MH+).

Workup

  1. customThe compound was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (95:5:0.5)
  2. temperatureincreasing in polarity to (90:10:1)
  3. customThe solvent was removed under reduced pressure
  4. customto give a residue which
  5. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-a7654215ce2e4a19ae651f0bb3ffc60b
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Linked notes

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