Urea → HCID 11585479, compound

HRID 2301597Notes

Reaction equation

HRID 2301597 reaction equation
NC(N)=O.[C:5]([O:9][C:10]([NH:12][CH:13]([C:31]([OH:33])=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][NH:18][S:19]([C:22]1[C:27]([Cl:28])=[CH:26][CH:25]=[C:24]([NH2:29])[C:23]=1[OH:30])(=[O:21])=[O:20])=[O:11])([CH3:8])([CH3:7])[CH3:6].[Br:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N:41]=[C:42]=[O:43]>>[Br:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:42]([NH:29][C:24]1[CH:25]=[CH:26][C:27]([Cl:28])=[C:22]([S:19]([NH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]([NH:12][C:10]([O:9][C:5]([CH3:8])([CH3:6])[CH3:7])=[O:11])[C:31]([OH:33])=[O:32])(=[O:20])=[O:21])[C:23]=1[OH:30])=[O:43]

Participants

4

Reactant 3

HCID 1176UreaHCID 1370972-Bromophenyl isocyanateHCID 18373463HCID 18373463, compound

Product 1

HCID 11585479HCID 11585479, compoundYield 7.3%

Procedure

Following the general procedure for urea formation outlined in example 15, N-[5-(tert-butoxycarbonylamino)-5-carboxypentyl]-3-amino-6-chloro-2-hydroxybenzenesulfonamide (189 mg, 0.42 mmol) and 2-bromophenylisocyanate (84 mg, 0.42 mmol) were coupled to form the desired urea (20 mg, 7%). LC-MS (m/z) 651.2 (M+).

Sources & evidence

ORD record
ord-780643a6a4284c90a8b0c6b4b8d0eb26
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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