Piperidine → [5-(1-Isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]-piperidin-1-yl-methanone

HRID 1437710Notes

Reaction equation

HRID 1437710 reaction equation
Cl.[CH:2]([N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[CH:20]=[C:19]([C:21]([OH:23])=O)[NH:18][C:15]3=[N:16][CH:17]=2)[CH2:7][CH2:6]1)([CH3:4])[CH3:3].F[B-](F)(F)F.[N:29]1(OC(N(C)C)=[N+](C)C)[C:33]2C=[CH:35][CH:36]=[CH:37][C:32]=2N=N1.N1CCCCC1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:2]([N:5]1[CH2:6][CH2:7][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[CH:20]=[C:19]([C:21]([N:29]4[CH2:35][CH2:36][CH2:37][CH2:32][CH2:33]4)=[O:23])[NH:18][C:15]3=[N:16][CH:17]=2)[CH2:9][CH2:10]1)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 684239235-(1-Isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid Hydrochloride

Product 1

HCID 16727358[5-(1-Isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]-piperidin-1-yl-methanoneYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 9, intermediate a), from 5-(1-isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid hydrochloride, O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, piperidine and N,N-diisopropylethylamine (7 eq.) in DMF to give the desired product as a light brown foam (51%).

Sources & evidence

ORD record
ord-8abe91ac01af4bb8a6b4c6dc7b848a06
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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