Acetic Acid → HCID 59410458, compound

HRID 1923486Notes

Reaction equation

HRID 1923486 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][C:5]2[CH:8]=[C:9]([C:12]3[C:13]([CH:17]=O)=[N:14][NH:15][N:16]=3)[CH:10]=[CH:11][C:4]=2[O:3]1.[F:19][C:20]([F:35])([F:34])[C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][C@H:28]2[CH3:33])=[N:25][CH:26]=1.C(O)(=O)C.B.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Na+].[Na+].[Na+]>CN(C=O)C>[F:35][C:20]([F:19])([F:34])[C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:17][C:13]3[C:12]([C:9]4[CH:10]=[CH:11][C:4]5[O:3][C:2](=[O:1])[NH:7][CH2:6][C:5]=5[CH:8]=4)=[N:16][NH:15][N:14]=3)[CH2:29][C@H:28]2[CH3:33])=[N:25][CH:26]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 57565333HCID 57565333, compoundHCID 59410475HCID 59410475, compoundHCID 178419192HCID 178419192, compound

Product 1

HCID 59410458HCID 59410458, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(3,4-dihydro-2-oxo-2H-benzo[e][1,3]oxazin-6-yl)-2H-1,2,3-triazole-4-carbaldehyde (15 mg, 0.06 mmol) and (R)-1-(5-(trifluoromethyl)pyridin-2-yl)-2-methylpiperazine (20 mg, 0.08 mmol) are mixed in DMF (1 ml) followed by addition of acetic acid (AcOH) (30 ul). The mixture is stirred at room temperature for 30 minute and then sodium triacetate boron hydride (42 mg, 0.2 mmol) is added. The resulting suspension is then stirred at room temperature overnight. The reaction is quenched using an aqueous saturated solution of sodium bicarbonate and then extracted with ethyl acetate (10 ml×4). The combined organic phase is concentrated and the resulting crude product is purified by HPLC giving 6-(5-(((R)-4-(5-(trifluoromethyl)pyridin-2-yl)-3-methylpiperazin-1-yl)methyl)-2H-1,2,3-triazol-4-yl)-3,4-dihydrobenzo[e][1,3]oxazin-2-one as a white powder. m/e:474 (M+1).

Workup

  1. stirringThe resulting suspension is then stirred at room temperature overnight
  2. customThe reaction is quenched
  3. extractionextracted with ethyl acetate (10 ml×4)
  4. concentrationThe combined organic phase is concentrated
  5. customthe resulting crude product is purified by HPLC

Sources & evidence

ORD record
ord-680816dfde4047258be05c6ce624113d
Source dataset
uspto-grants-2012_05
Patent number
US08178526B2

Reaction notes

Loading…