Hydrochloric Acid → HCID 23000576, compound

HRID 397536Notes

Reaction equation

HRID 397536 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][CH2:13][C:14]([F:22])([F:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[C:7]=1[F:23])C.[Li+].[OH-].Cl>CO>[F:22][C:14]([F:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH2:13][NH:12][C:8]1[C:7]([F:23])=[C:6]([CH2:5][C:4]([OH:24])=[O:3])[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 23000617HCID 23000617, compound

Product 1

HCID 23000576HCID 23000576, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.159 g (0.469 mmol) ethyl {2-[(2,2-difluoro-2-pyridin-2-ylethyl)amino]-3-fluoropyridin-4-yl}acetate 29-2 in 1 mL MeOH was added 469 uL (0.469 mmol, 1M aqueous solution) LiOH. The reaction was stirred at room temperature for 23 h. To the reaction was added 38.7 uL (0.469 mmol, 12M aqueous solution) HCl. The mixture was stirred for 10 min, concentrated in vacuo, and placed under vacuum alongside P2O5 to yield {2-[(2,2-difluoro-2-pyridin-2-ylethyl)amino]-3-fluoropyridin-4-yl}acetic acid 29-3. 1H NMR (CD3OD, 400 MHz) δ8.606 (d, 1H, J=4.77 Hz, ArH); 7.894 (t, 1H, J=7.83 Hz, ArH); 7.692 (d, 1H, J=7.69 Hz, ArH); 7.609 (d, 1H, J=5.22 Hz, ArH); 7.458 (t, 1H, J=6.05 Hz, ArH); 6.499 (t, 1H, J=4.99 Hz, ArH); 4.324 (t, 2H, J=13.92 Hz, CH2); 3.572 (s, 2H, CH2); MS (Electrospray): m/z 312.0 (M+H).

Workup

  1. stirringThe mixture was stirred for 10 min
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-198f21b679e444d284080381fd08e405
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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