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

HRID 405141
Notes
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Reaction equation

HRID 405141 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 710601375-(5-Chloro-2-(((4'-chloro-[1,1'-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinic acid

Product 1

HCID 71059954
Ethyl 3-(5-(5-chloro-2-(((4'-chloro-[1,1'-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes