4-Fluorobenzylamine → 5-(1-Isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid 4-fluoro-benzylamide

HRID 1437709Notes

Reaction equation

HRID 1437709 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](O)=[O:22])[NH:18][C:15]3=[N:16][CH:17]=2)[CH2:7][CH2:6]1)([CH3:4])[CH3:3].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[F:46][C:47]1[CH:54]=[CH:53][C:50]([CH2:51][NH2:52])=[CH:49][CH:48]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[F:46][C:47]1[CH:54]=[CH:53][C:50]([CH2:51][NH:52][C:21]([C:19]2[NH:18][C:15]3=[N:16][CH:17]=[C:12]([O:11][CH:8]4[CH2:9][CH2:10][N:5]([CH:2]([CH3:4])[CH3:3])[CH2:6][CH2:7]4)[CH:13]=[C:14]3[CH:20]=2)=[O:22])=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 673264-FluorobenzylamineHCID 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 167273575-(1-Isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic Acid 4-fluoro-benzylamideYield 37%

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, 4-fluorobenzylamine and N,N-diisopropylethylamine (7 eq.) in DMF to give the desired product as a light yellow solid (37%).

Sources & evidence

ORD record
ord-27dfa12356dc4bae85c3de5ce1f2b769
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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