Ethanol → HCID 178470738, compound

HRID 554671Notes

Reaction equation

HRID 554671 reaction equation
[CH:1]1([C:4]([N:6]([CH2:9][C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=2[C:20]2[CH:21]=[C:22]([CH2:28][C:29]([OH:31])=[O:30])[CH:23]=[N:24][C:25]=2[O:26]C)[CH2:7][CH3:8])=[O:5])[CH2:3][CH2:2]1.S(Cl)(Cl)=O.[CH3:36][CH2:37]O>C(Cl)Cl.O>[CH2:36]([O:31][C:29](=[O:30])[CH2:28][C:22]1[CH:23]=[N:24][C:25]([OH:26])=[C:20]([C:11]2[CH:12]=[CH:13][C:14]([C:16]([F:18])([F:19])[F:17])=[CH:15][C:10]=2[CH2:9][N:6]([C:4]([CH:1]2[CH2:2][CH2:3]2)=[O:5])[CH2:7][CH3:8])[CH:21]=1)[CH3:37]

Participants

6

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 45138482(5-{2-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid

Product 1

HCID 178470738HCID 178470738, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (5-{2-[(cyclopropanecarbonyl-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid (0.099 g, 0.22 mmol) in EtOH (1 mL) was added thionyl chloride (0.16 mL, 2.19 mmol), and the reaction was stirred at 80° C. overnight. The mixture was diluted with CH2Cl2 and H2O, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give (5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-hydroxy-pyridin-3-yl)-acetic acid ethyl ester. The ester was hydrolyzed to the acid as described in Example 3, Step 7.

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5813404ca161462dad468ab59067e465
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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