Triethylamine → HCID 58458928, compound

HRID 390343Notes

Reaction equation

HRID 390343 reaction equation
[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([OH:24])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:26][CH2:27][C:28](=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOCC>[CH2:1]([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:20])([CH3:21])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]([NH:26][CH2:27][C:28](=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 132906742-Propanone, 1-amino-3-(4-fluorophenyl)-, hydrochloride (1:1)HCID 210698583-(Benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid

Product 1

HCID 58458928HCID 58458928, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylic acid (prepared according to the procedure in Naidu, B. N. et al WO2005118593) (0.495 g, 1.5 mmol), 1-amino-3-(4-fluorophenyl)propan-2-one hydrochloride (prepared according to the procedure in Maeda, S. et al Chem. Pharm. Bull. 1984, 32, 2536-2543; 0.406 g, 2 mmol), HATU (0.760 g, 2 mmol), Et3N (0.56 mL, 4 mmol) and DMAP (60 mg) in DMF (15 mL) was stirred at room temperature. After 4 h, the reaction mixture was diluted with Et2O (100 mL), washed with water (3×10 mL), brine (10 mL), dried (Na2SO4), filtered and concentrated to give the title compound (0.57 g, 78% yield) as a viscous yellow oil which was used in the subsequent step without purification. 1HNMR (500 MHz, CDCl3) δ: 8.10-8.07 (1H, br s), 7.56 (2H, d, J=7.3 Hz), 7.34-7.28 (3H, m), 7.19 (2H, dd, J=8.6, 5.5 Hz), 7.03 (2H, t, J=8.6 Hz), 5.29 (2H, s), 4.30 (2H, d, J=4.9 Hz), 4.04-3.98 (4H, m), 3.75 (2H, s), 2.79 (6H, s), 1.62 (6H, s). HRMS (M+H) calcd for C26H27N3O5F: 480.1935. found: 480.1930.

Workup

  1. customprepared
  2. washwashed with water (3×10 mL), brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-42f30c9d31f645a7bb95a926fdab5f0a
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

Loading…