Benzoyl chloride → HCID 10212521, compound

HRID 897079Notes

Reaction equation

HRID 897079 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1([CH:16]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:17][NH:18][C:19]2[N:27]=[C:26]([CH2:28][NH:29][C:30]([NH:32][CH2:33][CH2:34][NH:35][CH:36]([CH3:38])[CH3:37])=[O:31])[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[C@@H:39]2[O:43][C@H:42]([C:44]([NH:46][CH2:47][CH3:48])=[O:45])[C@@H:41]([OH:49])[C@H:40]2[OH:50])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>C(OCC)(=O)C>[NH3:18].[C:1]([N:35]([CH:36]([CH3:37])[CH3:38])[CH2:34][CH2:33][NH:32][C:30]([NH:29][CH2:28][C:26]1[N:25]=[C:24]2[C:20]([N:21]=[CH:22][N:23]2[C@@H:39]2[O:43][C@H:42]([C:44]([NH:46][CH2:47][CH3:48])=[O:45])[C@@H:41]([OH:49])[C@H:40]2[OH:50])=[C:19]([NH:18][CH2:17][CH:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[N:27]=1)=[O:31])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 58904386HCID 58904386, compound

Product 2

HCID 222AmmoniaHCID 10212521HCID 10212521, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Benzoyl chloride (19 mg, 0.14 mmol) was added to a stirred solution of (2S,3S,4R,5R)-5-(6-[(2,2-diphenylethyl)amino]-2-{[({[2-(isopropylamino)ethyl]amino}carbonyl)amino]methyl}-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide (80 mg, 0.12 mmol) (Preparation 12) and triethylamine (0.034 ml, 0.25 mmol) in ethyl acetate (5 ml) and N′-methylpyrrolidinone (0.2 ml) at room temperature. The reaction mixture was stirred for 96 hours, washed with water (2 ml) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol 0.88 concentrated aqueous ammonia (90:10:1 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (80:20:3 by volume) to give the title compound as a foam (35 mg).

Workup

  1. washwashed with water (2 ml)
  2. customevaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol 0.88 concentrated aqueous ammonia (90:10:1 by volume) increasing in polarity to dichloromethane

Sources & evidence

ORD record
ord-d29220a0488547a5b9d1ff46b6521f29
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

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