1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86759542, compound

HRID 392898Notes

Reaction equation

HRID 392898 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:22]([C@@H:25]1[C@@H:29]([C:30](=[O:33])[NH:31][CH3:32])[O:28][C@@H:27]([N:34]2[CH:42]=[N:41][C:40]3[C:35]2=[N:36][CH:37]=[N:38][C:39]=3[NH:43][CH2:44][C:45]2[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:46]=2[O:47][CH2:48][C:49](O)=[O:50])[C@@H:26]1[OH:57])=[N+:23]=[N-:24].[NH:58]1[CH2:63][CH2:62][NH:61][CH2:60][C:59]1=[O:64]>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:32][NH:31][C:30]([C@@H:29]1[C@@H:25]([N:22]=[N+:23]=[N-:24])[C@@H:26]([OH:57])[C@H:27]([N:34]2[CH:42]=[N:41][C:40]3[C:35]2=[N:36][CH:37]=[N:38][C:39]=3[NH:43][CH2:44][C:45]2[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:46]=2[O:47][CH2:48][C:49](=[O:50])[N:61]2[CH2:62][CH2:63][NH:58][C:59](=[O:64])[CH2:60]2)[O:28]1)=[O:33]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 231360Piperazin-2-oneHCID 23523300HCID 23523300, compound

Product 1

HCID 86759542HCID 86759542, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

EDCI (44 mg, 0.23 mmol), HOBT (30 mg, 0.22 mmol) and DMAP (40 mg) were added to a mixture of (2R,3R,4S,5S)(2-{[9-(4-Azido-3-hydroxy-5-methylcarbamoyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-methyl}-4-chloro-phenoxy)-acetic acid (60 mg, 0.116 mmol) and piperizin-2-one (35 mg, 0.35 mmol) in anhydrous DMF (3 mL). After 20 hours at room temperature, the mixture was concentrated, pre-adsorbed onto silica gel and purified by flash chromatography (6-8% methanol/dichloromethane) to afford the title compound as a colorless solid. MS: 600 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated, pre-adsorbed onto silica gel
  2. custompurified by flash chromatography (6-8% methanol/dichloromethane)

Sources & evidence

ORD record
ord-e559db272d3140129247876c1809caa1
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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