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1,2-Cyclopropanedicarboxylic acid, trans- → trans-2-(4-(2,6-Dichlorobenzamido)pyridin-2-ylcarbamoyl)cyclopropanecarboxylic acid

HRID 449909
Notes
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Reaction equation

HRID 449909 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[CH:5]=[CH:4][N:3]=1.[C@@H:19]1([C:25](O)=[O:26])[CH2:21][C@H:20]1[C:22]([OH:24])=[O:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:17])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:25]([C@@H:19]2[CH2:21][C@H:20]2[C:22]([OH:24])=[O:23])=[O:26])[CH:7]=1)=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 69504501,2-Cyclopropanedicarboxylic acid, trans-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59618313N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide

Product 1

HCID 59617988trans-2-(4-(2,6-Dichlorobenzamido)pyridin-2-ylcarbamoyl)cyclopropanecarboxylic acidYield 67%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (141 mg, 0.50 mmol), trans-cyclopropane-1,2-dicarboxylic acid (325 mg, 2.5 mmol), and disiopropylethylamine (339 mg, 2.63 mmol) in dry DMF (5 mL) was added HATU (1951 mg, 2.5 mmol). The reaction mixture was heated at 70° C. for 6 hours and then quenched with sat. NH4Cl (100 mL). The mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by prep HPLC (10-50% CH3CN/H2O with 0.1% formic acid) to give trans-2-(4-(2,6-dichlorobenzamido)pyridin-2-ylcarbamoyl)cyclopropanecarboxylic acid (132 mg, 67% yield). 1H NMR (400 MHz, DMSO-d6) δ 11.14 (s, 1H), 10.86 (s, 1H), 8.38 (s, 1H), 8.23 (d, J=5.6 Hz, 1H), 7.62-7.55 (m, 2H), 7.54-7.45 (m, 2H), 1.90-1.82 (m, 1H), 1.25 (dt, J=8.0, 5.4 Hz, 3H). LCMS (ESI) m/z: 394.0 [M+H+].

Workup

  1. customquenched with sat. NH4Cl (100 mL)
  2. extractionThe mixture was extracted with EtOAc (3×100 mL)
  3. dry with materialThe combined organic extracts were dried with Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by prep HPLC (10-50% CH3CN/H2O with 0.1% formic acid)

Sources & evidence

ORD record
ord-13fb0baad3b6493383d1043c18e0046a
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486950B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes