Diisopropylethylamine → Ethyl 3-(5-(5-chloro-2-(((4'-chloro-[1,1'-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinamido)propanoate

HRID 405141Notes

Reaction equation

CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:41][N:42]([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=3)=[CH:46][CH:45]=2)[CH3:43])=[C:30]([C:32]2[CH:33]=[CH:34][C:35]([C:38](O)=[O:39])=[N:36][CH:37]=2)[CH:31]=1.CCN(C(C)C)C(C)C.Cl.[CH2:67]([O:69][C:70](=[O:74])[CH2:71][CH2:72][NH2:73])[CH3:68]>CCOC(C)=O.C1COCC1>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:41][N:42]([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:51]=[CH:52][C:53]([Cl:56])=[CH:54][CH:55]=3)=[CH:46][CH:45]=2)[CH3:43])=[C:30]([C:32]2[CH:33]=[CH:34][C:35]([C:38]([NH:73][CH2:72][CH2:71][C:70]([O:69][CH2:67][CH3:68])=[O:74])=[O:39])=[N:36][CH:37]=2)[CH:31]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Solid HATU (127 mg, 0.34 mmol) was added to a THF solution (3 mL) of 5-(5-chloro-2-(((4′-chloro-[1,1′-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinic acid (155 mg, 0.34 mmol), i-Pr2NEt (0.29 mL, 1.67 mmol), and β-alanine ethyl ester hydrochloride (54 mg, 0.35) and the resulting mixture was warmed to 45° C. After 16 h the resulting mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

washwashed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
custompurified via column chromatography

Sources & evidence

ORD record: ord-f244abd10ffa44a2bc1d33d38288ef8a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Reaction notes

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