Diisopropylethylamine → HCID 178521696, compound

HRID 1794956Notes

Reaction equation

HRID 1794956 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][C:15]1=[O:20])(=[O:13])=[O:12])([O-:4])=[O:3].[CH:21]([O:34][C:35]([NH:37][C:38]1[N:46]=[CH:45][N:44]=[C:43]2[C:39]=1[N:40]=[CH:41][N:42]2CC(O)=O)=[O:36])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1CN([P+]([O:67]N2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N([CH2:91][CH3:92])C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C.O>[CH:21]([O:34][C:35]([NH:37][C:38]1[N:46]([CH2:92][C:91]([N:17]2[CH2:18][CH2:19][N:14]([S:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N+:2]([O-:4])=[O:3])(=[O:12])=[O:13])[C:15](=[O:20])[CH2:16]2)=[O:67])[CH:45]=[N:44][C:43]2[C:39]=1[N:40]=[CH:41][N:42]=2)=[O:36])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 15513044(6-{[(Diphenylmethoxy)carbonyl]amino}-9H-purin-9-yl)acetic acidHCID 688024401-(2-Nitrobenzenesulfonyl)-piperazin-2-one HCl salt

Product 1

HCID 178521696HCID 178521696, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt (0.76 g, 2.36 mmol), [6-N-(benzhydryloxycarbonyl)-adenin-9-yl]-acetic acid (1.0 g, 2.47 mmol), and PyBOP (1.35 g) in DMF (20 mL) was added N,N-diisopropylethylamine (0.95 mL) at 5° C. After stirring for additional 2 h, the reaction mixture was diluted with ethyl acetate (200 mL) and water (150 mL). The organic layer was separated and washed with water, 5% aqueous sodium bicarbonate, 10% aqueous citric acid, and brine. The organic layer was dried over sodium sulfate and concentrated in reduced pressure. The residue was purified by column chromatography to give the title compound (830 mg, 58%). 1H NMR (DMSO-d6) δ 10.95 (s, 1H), 8.59 (s, 0.6H), 8.58 (s, 0.4H), 8.40˜8.36 (m, 1H), 8.33 (s, 0.6H), 8.31 (s, 0.4H), 8.14 (d, 1H), 8.06˜7.96 (m, 2H), 7.54˜7.27 (m, 10H), 6.82 (s, 1H), 5.39 (s, 1.2H), 5.30 (s, 0.8H), 4.56 (s, 0.8H), 4.27 (s, 1.2H), 4.12˜4.08 (m, 2.4H), 3.92˜3.86 (m, 1.6H).

Workup

  1. customThe organic layer was separated
  2. washwashed with water, 5% aqueous sodium bicarbonate, 10% aqueous citric acid, and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-575a04a7162d4c898b996208cb6819ad
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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