1,1'-Carbonyldiimidazole → HCID 67019329, compound

HRID 1697030Notes

Reaction equation

HRID 1697030 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[N:15]=[C:14]3[C:10]([N:11]=[CH:12][N:13]3[C@H:16]3[C@@H:20]4[O:21][C:22]([CH3:25])([CH3:24])[O:23][C@@H:19]4[C@@H:18]([NH:26][C:27](=[O:30])[CH2:28][CH3:29])[CH2:17]3)=[C:9]([NH:31][CH2:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:8]=2)[CH2:3]1.[CH:46]1[N:50]=[CH:49][N:48]([C:51](N2C=NC=C2)=[O:52])[CH:47]=1>C(Cl)Cl>[CH3:24][C:22]1([CH3:25])[O:23][C@@H:19]2[C@@H:18]([NH:26][C:27](=[O:30])[CH2:28][CH3:29])[CH2:17][C@@H:16]([N:13]3[CH:12]=[N:11][C:10]4[C:14]3=[N:15][C:7]([N:4]3[CH2:5][CH2:6][C@@H:2]([NH:1][C:51]([N:48]5[CH:47]=[CH:46][N:50]=[CH:49]5)=[O:52])[CH2:3]3)=[N:8][C:9]=4[NH:31][CH2:32][CH:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:20]2[O:21]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66629700N-{(3aR,4S,6R,6aS)-6-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-yl}-propionamide

Product 1

HCID 67019329HCID 67019329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture comprising N-{(3aR,4S,6R,6aS)-6-[2-((R)-3-amino-pyrrolidin-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl}-propionamide (see preparation of intermediates) (0.24 g, 0.39 mmol) and CDI (0.275 g, 1.7 mmol) in DCM is stirred at room temperature for 3 hours. Purification of the resulting mixture by chromatography on silica eluting with 0-5% MeOH in DCM yields the titled compound as a yellow oil. The compound exists as a mixture of the imidazole-urea intermediate together with variable amounts of the corresponding isocyanate and imidazole which are equally suitable as precursors to ureas.

Workup

  1. customPurification of the resulting mixture by chromatography on silica eluting with 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-e56ea2f66bc94b99a23eca880d415af1
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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