Diisopropylethylamine → HCID 57542564, compound

HRID 2080297Notes

Reaction equation

HRID 2080297 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[CH2:17][CH2:18][NH2:19].CCN(C(C)C)C(C)C>CC#N>[Cl:11][C:9]1[C:8]([F:12])=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:19][CH2:18][CH2:17][C:16]2[CH:20]=[CH:21][CH:22]=[C:14]([F:13])[CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5339282-(3-Fluorophenyl)ethanamineHCID 27336592,6-Dichloro-5-fluoronicotinic acid

Product 1

HCID 57542564HCID 57542564, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,6-dichloro-5-fluoronicotinic acid (1.26 g, 6.0 mmol), 3-fluorophenethyl amine (1.25 mL, 9.0 mmol), DIEA (3.14 mL, 18 mmol) and MeCN (6 mL) was refluxed for 48 hrs and concentrated. The residue was dissolved in EtOAc (120 mL) and washed with saturated citric acid, water, brine, dried and concentrated. The organic layers were combined, dried (MgSO4) and concentrated. The residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give 6-chloro-5-fluoro-2-(3-fluorophenethylamino)nicotinic acid as a solid (920 mg, 49%). LRMS (M+H+) m/z 313.0.

Workup

  1. temperaturewas refluxed for 48 hrs
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc (120 mL)
  4. washwashed with saturated citric acid, water, brine
  5. customdried
  6. concentrationconcentrated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified on RP-HPLC
  10. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-366190be76f84433adf8d1092f3cba98
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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