Urea → HCID 86613588, compound

HRID 1365507Notes

Reaction equation

[NH2:1][C@:2]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1)([C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([F:17])[CH:8]=1)[CH2:3][C:4]([NH2:6])=[O:5].[NH2:25][C:26](N)=[O:27]>>[NH2:6][C:4](=[O:5])[CH2:3][C@@:2]([NH:1][C:26]([NH:25][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:17])[CH:8]=1)=[O:27])([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1)[C:7]1[CH:12]=[C:11]([C:13]([F:15])([F:14])[F:16])[CH:10]=[C:9]([F:17])[CH:8]=1

Participants

Reactant 2

HCID 1176Urea

HCID 66934364HCID 66934364, compound

Product 1

HCID 86613588HCID 86613588, compoundYield 56%

Procedure

(S)-3-amino-3-(5-chloropyridin-2-yl)-3-(3-fluoro-5-(trifluoromethyl)phenyl) propanamide (0.031 g, 0.085 mmol) was converted to the urea as described in Procedure 2. (S)-1-(3-amino-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-3-oxopropyl)-3-(3-fluorophenyl)urea (0.023 g, 56% yield) was isolated after purification by reverse phase prep HPLC: YMC ODSA 30×100 mm, 20-100% MeOH/H2O (0.1% TFA) gradient over 10 min, flow rate 20 mL/min eluting at a retention time of 10.3 min. LCMS: 1.98 min [M+1] 499.1 (2 min gradient, MeOH/H2O 0.1% TFA).

Sources & evidence

ORD record: ord-722c4669fa3149cf8b19f56fda19dcc2
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888376B2

Reaction notes

Loading…