Triethylamine → HCID 178429277, compound

HRID 2427834Notes

Reaction equation

HRID 2427834 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]2[NH:9][N:10]=[C:11]([OH:12])[C:3]=12.[F:13][C:14]([F:25])([F:24])[CH:15]1[CH2:20][CH2:19][N:18]([C:21](Cl)=[O:22])[CH2:17][CH2:16]1.C(N(CC)CC)C>N1C=CC=CC=1>[OH:8][C:6]1[N:5]=[C:4]2[NH:9][N:10]=[C:11]([O:12][C:21]([N:18]3[CH2:17][CH2:16][CH:15]([C:14]([F:24])([F:13])[F:25])[CH2:20][CH2:19]3)=[O:22])[C:3]2=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 798870814-(Trifluoromethyl)piperidine-1-carbonyl chlorideHCID 178429275HCID 178429275, compound

Product 1

HCID 178429277HCID 178429277, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Methyl-1H-pyrazolo[3,4-b]pyridine-3,6-diol (1 g, 6.05 mmol), 4-trifluoromethyl-piperidine-1-carbonyl chloride (1.436 g, 6.6 mmol) and triethylamine (1.68 ml, 12.11 mmol) were stirred in 25 ml of pyridine at room temp for 1 h. Addition of 0.5 ml of triethylamine was followed by stirring for 2 h, concentration and addition of ethyl acetate and water. The resulting precipitate was filtered off with suction and dried. Yield: 765 mg (37%) of 4-trifluoromethylpiperidine-1-carboxylic acid 6-hydroxy-4-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl ester. The organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 96 mg (5%) of 4-trifluoromethylpiperidine-1-carboxylic acid 6-hydroxy-4-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl ester. M+H+: 345.13; 102 mg (3%) of 4-trifluoromethylpiperidine-1-carboxylic acid 4-methyl-3-(4-trifluoromethylpiperidine-1-carbonyloxy)-1H-pyrazolo[3,4-b]pyridin-6-yl ester, M+H+: 524.20; 106 mg (3%) of 4-trifluoromethylpiperidine-1-carboxylic acid 6-hydroxy-4-methyl-1-(4-trifluoromethylpiperidine-1-carbonyl)-1H-pyrazolo[3,4-b]pyridin-3-yl ester, M+H+: 524.52; 54 mg (1.3%) of 4-trifluoromethylpiperidine-1-carboxylic acid 4-methyl-3-(4-trifluoromethylpiperidine-1-carbonyloxy)-1-(4-trifluoromethylpiperidine-1-carbonyl)-1H-pyrazolo[3,4-b]pyridin-6-yl ester, M+H+: 703.36.

Workup

  1. concentrationconcentration and addition of ethyl acetate and water
  2. filtrationThe resulting precipitate was filtered off with suction
  3. customdried
  4. customThe organic phase was separated off
  5. concentrationconcentrated
  6. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-e490e1775df845a69425a51e0d23fb76
Source dataset
uspto-grants-2011_06
Patent number
US07968719B2

Reaction notes

Loading…