4-Fluorobenzylamine → HCID 54681995, compound

HRID 720294Notes

Reaction equation

HRID 720294 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C([O:12][C:13]([C:15]1[N:16]=[C:17]([N:24]2[CH2:29][CH2:28][CH:27]([O:30]C(=O)C(F)(F)F)[CH2:26][CH2:25]2)[N:18]([CH3:23])[C:19](=[O:22])[C:20]=1[OH:21])=O)C>CN(C)C=O>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:13]([C:15]2[N:16]=[C:17]([N:24]3[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]3)[N:18]([CH3:23])[C:19](=[O:22])[C:20]=2[OH:21])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 58739080HCID 58739080, compound

Product 1

HCID 54681995HCID 54681995, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-fluorobenzylamine (156 mg, 1.25 mmol) and 5-hydroxy-1-methyl-6-oxo-2-[4-(2,2,2-trifluoroacetoxy)piperidin-1-yl]-1,6-dihydropyrimidine-4-carboxylic acid ethyl ester (100 mg, 0.254 mmol) in dimethylformamide (3 mL) was heated at 120° C. for 2 h. Then, cooled and purified by preparative HPLC using MeOH/Water containg 0.1% TFA as an eluent. The fractions containing the product were combined and concentrated to afford title compound as a off-white solid (46 mg, 48%). 1H NMR (500 MHz, CDCl3) δ: 11.62 (s, 1H), 7.75 (br s, 1H), 7.31–7.28 (m, 2H), 7.04 (t, J=8.7 Hz, 2H), 4.56 (d, J=6.4 Hz, 2H), 3.95–3.89 (m, 1H), 3.52 (s, 3H), 3.28–3.23 (m, 2H), 2.88–2.83 (m, 2H), 2.02–1.96 (m, 2H), 1.73–1.66 (m, 2 H), 1.54 (br s, 1H). HRMS (M−H) calcd for C18H20FN4O4: 375.1469. found: 375.1472. Anal cald for C18H21FN4O4: C, 57.44; H, 5.62; N, 14.88. Found: C, 57.19; H, 5.55; N, 14.82.

Workup

  1. temperatureThen, cooled
  2. custompurified by preparative HPLC
  3. additionThe fractions containing the product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-93c8be0f9dbe4943bb3ead88ba152885
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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