3-Fluoro-4-hydroxybenzaldehyde → HCID 87954412, compound

HRID 897253Notes

Reaction equation

HRID 897253 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[OH:31])[CH:26]=O>>[ClH:1].[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[OH:31])[CH2:26][N:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:7]2[C:6]3[C:11](=[CH:12][CH:13]=[C:4]([O:3][CH3:2])[CH:5]=3)[O:10][C:9](=[O:14])[CH:8]=2)[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 5872503-Fluoro-4-hydroxybenzaldehydeHCID 22348292HCID 22348292, compound

Product 1

HCID 87954412HCID 87954412, compoundYield 95.4%

Procedure

According to Procedure C above, (I) (0.0223 g; 0.081 mmol) and 3-fluoro-4-hydroxy-benzaldehyde were allowed to react to give after the purification the corresponding mono-TFA salt. The product was then suspended in MeOH and hydrochloride salt was precipitated by addition of 4 N HCl solution in dioxane. The resulting white solid was triturated with Et2O/MeOH (2:1), washed with Et2O and dried under high vacuum to afford 33.6 mg (95.4%) of the title compound. MS (DCI/NH3)(+)Q1MS m/z 399 (M+H)+; 1H NMR (500 MHz, pyridine-d5) δ ppm 1.94 (m, 2H), 2.10 (m, 2H), 2.27 (m, 2H), 3.06 (m, 2H), 3.42 (s, 3H), 3.61 (m, 1H), 3.65 (s, 2H), 5.71 (s, 1H), 7.15 (m, 2H), 7.24 (m, 1H), 7.33 (d, J=9.05 Hz, 1H), 7.39 (m, 1H), 7.69 (m, 1H+1N H).

Workup

  1. customto react
  2. customto give
  3. customafter the purification the corresponding mono-TFA salt
  4. customhydrochloride salt was precipitated by addition of 4 N HCl solution in dioxane
  5. customThe resulting white solid was triturated with Et2O/MeOH (2:1)
  6. washwashed with Et2O
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-b6c29821385343cea541c350bcd0c061
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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