Glycolic Acid → HCID 117987622, compound

HRID 2206251Notes

Reaction equation

HRID 2206251 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([O:18][CH3:19])[C:12]=2[C:11]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:22][CH:21]=2)=[N:10]1.[OH:32][CH2:33][C:34](O)=[O:35].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[C:13]([O:18][CH3:19])[C:12]=2[C:11]([C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH2:27][CH2:28][N:29]([C:33](=[O:32])[CH2:34][OH:35])[CH2:30][CH2:31]3)=[CH:24][CH:25]=2)=[N:10]1

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117988120HCID 117988120, compound

Product 1

HCID 117987622HCID 117987622, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2,6-difluorophenyl)-4-methoxy-3-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[4,3-c]pyridine (220 mg) obtained in Step D of Example 311, 2-hydroxyacetic acid (42 mg) and triethylamine (158 mg) in anhydrous THF (5 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (297 mg) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the residue was purified by thin layer silica gel chromatography (ethyl acetate) to give the title compound (220 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe residue was purified by thin layer silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-d888be5d2a2547719b3e4777e01a959d
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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