Triethylamine → HCID 58739064, compound

HRID 720279Notes

Reaction equation

HRID 720279 reaction equation
[O:1]=[S:2]1(=[O:21])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:9]([CH3:20])[C:10](=[O:19])[C:11]([O:17][CH3:18])=[C:12]([C:14]([OH:16])=O)[N:13]=1.[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>C(#N)C.C(OCC)(=O)C>[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:28][C:14]([C:12]2[N:13]=[C:8]([N:3]3[CH2:4][CH2:5][CH2:6][CH2:7][S:2]3(=[O:1])=[O:21])[N:9]([CH3:20])[C:10](=[O:19])[C:11]=2[O:17][CH3:18])=[O:16])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 2724699PyBOPHCID 58739076HCID 58739076, compound

Product 1

HCID 58739064HCID 58739064, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-5-methoxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid (0.235 g, 0.74 mmol) and 4-fluorobenzylamine (0.14 g, 1.13 mmol) in acetonitrile (10 ml) was treated at 22° C. with triethylamine (0.32 ml, 2.3 mmol) followed by benzotriazole-1-yloxy-tris-pyrrolidino-phosphonium hexafluorophosphate (0.42 g, 0.81 mmol) and the resulting mixture was stirred for 3 h. The reaction mixture was then diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 1:1 to ethyl acetate) gave 0.291 g (92% yield) of the title amide as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.6–1.7 and 2.3–2.5 (4H, m, 2×CH2), 3.2 and 3.5 (2×1H, m, CH2), 3.62 (3H, s, NCH3), 3.7 and 3.95 (2×1H, m, CH2), 4.04 (3H, s, OCH3), 4.59 (2H, d, J=5.8 Hz, NCH2), 7.04 (2H, m, aromatics), 7.31 (2H, m, aromatics), 7.75 (1H, broad, NH). HRMS (FAB POS) calculated for C18H22FN4O5S [M+H+]: 425.129495. found: 425.129040.

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-bc8c66f5aab0407c85ecf7cdd5995915
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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