Glycolic Acid → HCID 86711934, compound

HRID 1475242Notes

Reaction equation

HRID 1475242 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[C:10]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=3)[N:21]=2)[N:3]=1.[OH:36][CH2:37][C:38](O)=[O:39].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[OH:39][CH2:38][C:37]([N:17]1[CH2:16][CH2:15][N:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][N:6]3[C:2]([CH3:1])=[N:3][C:4]([C:20]4[O:24][N:23]=[C:22]([C:25]5[CH:30]=[CH:29][C:28]([O:31][C:32]([F:33])([F:35])[F:34])=[CH:27][CH:26]=5)[N:21]=4)=[N:5]3)[CH:9]=2)[CH2:19][CH2:18]1)=[O:36]

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86711932HCID 86711932, compound

Product 1

HCID 86711934HCID 86711934, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(5-methyl-1-(3-(piperazin-1-yl)benzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (Example 81; 110 mg, 0.23 mmol), 2-hydroxyacetic acid (21 mg, 0.28 mmol) and DIPEA (89 mg, 0.69 mmol) in DMF (5 mL) was added HATU (106 mg, 0.28 mmol). The resulting mixture was stirred at room temperature for 3 h, diluted with H2O (10 mL) and extracted with EtOAc (2×10 mL). The combined organic layers were washed with H2O (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure; the residue was purified by prep-HPLC (20% to 50% MeCN/H2O containing 0.1% trifluoroacetic acid) to give the title compound as a white solid; MS (ES+) C25H24F3N7O4 requires: 543. found: 544 [M+H]+; 1H-NMR (500 MHz, DMSO-d6) δ 8.23 (d, J=8.5 Hz, 2H), 7.62 (d, J=8.5 Hz, 2H), 7.24 (m, 1H), 6.95 (m, 2H), 6.69 (d, J=7.5 Hz, 1H), 5.49 (s, 2H), 4.12 (s, 2H), 3.56 (m, 2H), 3.15 (m, 4H), 2.58 (s, 3H), 2.50 (m, 2H).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe combined organic layers were washed with H2O (10 mL) and brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by prep-HPLC (20% to 50% MeCN/H2O containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-2b2d87e18aad4d1fa493a346f32573c6
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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