Diisopropylethylamine → 5Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-oxo-2-(4-trifluoromethylpiperidin-1-yl)ethyl]amide

HRID 751720Notes

Reaction equation

HRID 751720 reaction equation
[F:1][C:2]([F:10])([F:9])[CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[Cl:11][C:12]1[CH:13]=[C:14]2[CH:20]=[C:19]([C:21]([NH:23][C@@H:24]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:25](O)=[O:26])=[O:22])[NH:18][C:15]2=[CH:16][N:17]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][C@H:24]([NH:23][C:21]([C:19]2[NH:18][C:15]3=[CH:16][N:17]=[C:12]([Cl:11])[CH:13]=[C:14]3[CH:20]=2)=[O:22])[C:25](=[O:26])[N:6]2[CH2:7][CH2:8][CH:3]([C:2]([F:10])([F:9])[F:1])[CH2:4][CH2:5]2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1364694-(Trifluoromethyl)piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 597536992-(S)-[(5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionic acid

Product 1

HCID 114433575Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-oxo-2-(4-trifluoromethylpiperidin-1-yl)ethyl]amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 4-trifluoromethyl piperidine (17 mg, 0.11 mmol) was added a solution of 2-(S)-[(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propionic acid (EXAMPLE 228, 40 mg, 0.11 mmol) in DMF (400 μL) followed by a solution of HATU (50 mg, 0.13 mmol) in DMF (400 μL) and finally a solution of DIPEA (23 μL, 0.13 mmol) in DMF (200 μL). The resulting mixture was stirred at rt for 96 h then solvent was removed in vacuo. The crude material was purified by crystallisation from THF/petroleum ether to give the title compound as a yellow powder. (ES+)=497.23 [M+H]+; RT=3.50 min.

Workup

  1. customsolvent was removed in vacuo
  2. customThe crude material was purified by crystallisation from THF/petroleum ether

Sources & evidence

ORD record
ord-774cb99e318e45e8ad91726ce2dd3957
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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