Urea → HCID 68547768, compound

HRID 2243505Notes

Reaction equation

HRID 2243505 reaction equation
NC(N)=O.[CH2:5]([N:7]=[C:8]=[O:9])[CH3:6].[CH3:10][O:11][C:12]([C:14]1[S:33][C:17]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([NH:25][CH2:26][CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:23]=3[S:24][C:16]=2[C:15]=1[O:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:13]>CN(C1C=CN=CC=1)C.ClCCCl>[CH3:10][O:11][C:12]([C:14]1[S:33][C:17]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([N:25]([CH2:26][CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:8]([NH:7][CH2:5][CH3:6])=[O:9])[C:23]=3[S:24][C:16]=2[C:15]=1[O:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:13]

Participants

6

Reactant 3

HCID 1176UreaHCID 8022Ethyl isocyanateHCID 68548829HCID 68548829, compound

Product 1

HCID 68547768HCID 68547768, compoundYield 43.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Step B Urea Formation: Addition of ethyl isocyanate (0.5 mL, 6.5 mmol) to 7-(Cyclohexylmethyl-amino)-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester (60 mg, 0.13 mmol) was carried out following a procedure similar to that delineated in Step B, Example 27, with the following exceptions: co-solvent (DCE), addition of catalytic DMAP, temperature (70° C. vs. ambient), and total reaction time (100+ hours), affording 30 mg of 7-(1-Cyclohexylmethyl-3-ethyl-ureido)-1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester (43% yield).

Sources & evidence

ORD record
ord-f1353619fa904908897373e187ccc11e
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

Loading…