Triethylamine → 1-[3-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-2H-pyrazolo[3,4-c]pyridin-7-yl]-4-ethylaminopiperidine-4-carboxylic Acid Amide

HRID 915852Notes

Reaction equation

HRID 915852 reaction equation
Cl[C:2]1[C:7]2=[N:8][N:9]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:6]2[CH:5]=[CH:4][N:3]=1.[CH2:26]([NH:28][C:29]1([C:35]([NH2:37])=[O:36])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:27].C(N(CC)CC)C>C(O)C>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[N:8]=[C:7]3[C:6]=2[CH:5]=[CH:4][N:3]=[C:2]3[N:32]2[CH2:31][CH2:30][C:29]([NH:28][CH2:26][CH3:27])([C:35]([NH2:37])=[O:36])[CH2:34][CH2:33]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 965734-(Ethylamino)piperidine-4-carboxamideHCID 589595107-Chloro-3-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-2H-pyrazolo[3,4-c]pyridine

Product 1

HCID 117531041-[3-(4-Chlorophenyl)-2-(2,4-dichlorophenyl)-2H-pyrazolo[3,4-c]pyridin-7-yl]-4-ethylaminopiperidine-4-carboxylic Acid Amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

7-Chloro-3-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-2H-pyrazolo[3,4-c]pyridine (I-1A-1c; 71 mg, 0.17 mmol), 4-ethylaminopiperidine-4-carboxylic acid amide (I-1A-1f; 62 mg, 0.36 mmol) and triethylamine (52 microliters, 0.52 mmol) were combined in ethanol (1.2 ml) and the heterogeneous mixture was stirred and heated to 60° C. After 3 days, the reaction was cooled to room temperature and purified on a Biotage™ Flash 12M column using a solvent gradient of 0-2-4-6% methanol in methylene chloride as eluant to afford title compound I-1A-1 (73 mg, 78%) as a glass: +ESI MS (M+1) 543.1; 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=2.1 Hz, 1H), 7.60 (d, J=8.7 Hz, 1H), 7.57 (d, J=6.2 Hz, 1H), 7.49 (dd, J=8.3, 2.1 Hz, 1H), 7.38 (d, J=8.3 Hz, 2H), 7.26 (d, J=8.3 Hz, 2H), 6.84 (d, J=6.2 Hz, 1H), 4.35-4.28 (m, 2H), 4.10 (ddd, J=13.3, 9.1, 3.3 Hz, 2H), 2.51 (q, J=7.1 Hz, 2H), 2.12 (ddd, J=13.7, 9.1, 3.7 Hz, 2H), 1.73 (dq, J=13.3, 3.3 Hz, 2H), 1.10 (t, J=7.1 Hz, 3H).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. custompurified on a Biotage™ Flash 12M column

Sources & evidence

ORD record
ord-bea30ac1f6e84121910b1251ff875e02
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

Loading…