Hydrochloric Acid → HCID 23000586, compound

HRID 397538Notes

Reaction equation

HRID 397538 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][CH2:13][C:14]([F:23])([F:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=2[O-:21])[C:7]=1[F:24])C.[Li+].[OH-].Cl>CO>[F:23][C:14]([F:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N+:16]=1[O-:21])[CH2:13][NH:12][C:8]1[C:7]([F:24])=[C:6]([CH2:5][C:4]([OH:25])=[O:3])[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 59085882HCID 59085882, compound

Product 1

HCID 23000586HCID 23000586, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.064 g (0.18 mmol) ethyl(2-{[2,2-difluoro-2-(1-oxidopyridin-2-yl)ethyl]amino}-3-fluoropyridin-4-yl)acetate 30-2 in 1 mL MeOH was added 198 uL (0.198 mmol, 1M aqueous solution) LiOH. The reaction was stirred at room temperature for 19 h. To the mixture was added 36 uL (0.036 mmol, 1M aqueous solution). After an additional 24 h, 54 uL (0.054 mmol, 1M aqueous solution) more LiOH was added. After an another 4 h at room temperature, 23.8 uL (0.288 mmol, 12M aqueous solution) HCl was added. The reaction was stirred for 5 min and then concentrated in vacuo to give (2-{[2,2-difluoro-2-(1-oxidopyridin-2-yl)ethyl]amino}-3-fluoropyridin-4-yl)acetic acid 30-3. 1H NMR (CD3OD, 400 MHz) δ8.426 (d, 1H, J=5.86 Hz, ArH); 7.765 (dd, 1H, J=2.34 Hz, 7.37 Hz, ArH); 7.628-7.565 (m, 3H, ArH); 6.646 (t, 1H, J=5.36 Hz, ArH); 4.636 (t, 2H, J=13.60 Hz, CH2); 3.659 (s, 2H, CH2); MS (Electrospray): m/z 328.0 (M+H).

Workup

  1. waitAfter an additional 24 h
  2. stirringThe reaction was stirred for 5 min
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84965a9f288a47aa82206e3b643ff834
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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