Triethylamine → HCID 178429277, compound

HRID 490311Notes

Reaction equation

HRID 490311 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-3aa417b2ac9a40e5b80837bf641e301b
Source dataset
uspto-grants-2009_05
Patent number
US07528155B2

Reaction notes

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