Hydrochloric Acid → HCID 67041575, compound

HRID 62723

Reaction equation

HRID 62723 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:14])[C:10]=1[O:11][CH2:12][CH3:13])[C:5]([OH:7])=O.CC[N:17]([CH:21]([CH3:23])[CH3:22])C(C)C.CN(C([O:31]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:48]([O:50][C:51]1C(C(F)(F)F)=C[C:54]([N+]([O-])=O)=[CH:53][C:52]=1[C:64](F)(F)F)C.Cl>CN(C=O)C>[Cl:14][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([Cl:1])[C:10]=1[O:11][CH2:12][CH3:13])[C:5]([NH:17][C:21]1[CH:22]=[CH:64][C:52]([C:51]([O:50][CH3:48])=[O:31])=[C:53]([CH3:54])[CH:23]=1)=[O:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 8201383,5-Dichloro-4-ethoxybenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86666595HCID 86666595, compound

Product 1

HCID 67041575HCID 67041575, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3,5-dichloro-4-ethoxybenzoic acid (1) (285 mg, 1.21 mmol) and DIPEA (1.05 mL, 6.05 mmol) in DMF (2.5 mL) was added to HATU (690 mg, 1.82 mmol) and the orange mixture was stirred for 5 min prior to the addition of methyl 4-amino-2-methylbenzoate (2) (200 mg, 1.21 mmol) in DMF (1 mL). The resulting dark orange solution was stirred overnight for 18 h. 2 M HCl (10 mL) was added and stirring continued for 10 min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3×15 mL), dried over MgSO4, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to afford methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3) (267 mg, 56%): m/z 380 (M−H)− (ES−). 1H NMR (400 MHz, CDCl3) δ: 7.97 (1H, s), 7.80 (3H, m), 7.54 (1H, dd), 7.51 (1H, d), 4.18 (2H, q), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t).

Workup

  1. stirringThe resulting dark orange solution was stirred overnight for 18 h
  2. stirringstirring
  3. waitcontinued for 10 min
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe organic layer was washed with water (3×15 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuo
  9. customThe yellow residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane)

Sources & evidence

ORD record
ord-632a4c8a5af245d3bd79e7bb8d9e8145
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Linked notes

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