Benzoic Acid → HCID 45275135, compound

HRID 1622348Notes

Reaction equation

HRID 1622348 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[CH:15][C:14]=2[Cl:20])[CH2:9][CH2:8]1)=[O:6].[C:21](O)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:21]([NH:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:8][CH2:9][N:10]([C:13]2[C:14]([Cl:20])=[CH:15][N:16]=[CH:17][C:18]=2[Cl:19])[CH2:11][CH2:12]1)=[O:6])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45275021HCID 45275021, compound

Product 1

HCID 45275135HCID 45275135, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-aminoethyl)-1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide E13 (50 mg, 0.16 mmol), benzoic acid (23 mg, 0.19 mmol) and HATU (72 mg, 0.19 mmol) in DMF (1 mL) was added DIPEA (82 μL, 0.47 mmol). After 16 h the mixture was poured into a saturated solution of sodium hydrogen carbonate (50 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were washed with water (50 mL), a saturated solution of citric acid (50 mL) water (50 mL) and brine (50 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 9:1) to furnish the title compound as a white solid (24 mg, 36%), m.p. 209-211° C.; umax (CHCl3)/cm−1 3029, 3006, 1656, 1523, 1385, 1228, 1017; m/z (ESI) C20H22Cl2N4NaO2 requires 443.1012, found [M+Na]+ 443.1013.

Workup

  1. extractionextracted with EtOAc (2×25 mL)
  2. washThe combined organic extracts were washed with water (50 mL)
  3. dry with materiala saturated solution of citric acid (50 mL) water (50 mL) and brine (50 mL), dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 9:1)

Sources & evidence

ORD record
ord-816a247d82284d598d99e590c716d3e0
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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