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

HRID 1437711Notes

Reaction equation

HRID 1437711 reaction equation
FC1(F)[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:28][C:13]3=[N:14][CH:15]=[C:16]([O:18][CH:19]4[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]4)[CH:17]=[C:12]3[CH:11]=2)=[O:9])[CH2:4][CH2:3]1.F[B-](F)(F)F.N1([O:44]C(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.N1CCOCC1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:25]([N:22]1[CH2:23][CH2:24][CH:19]([O:18][C:16]2[CH:17]=[C:12]3[CH:11]=[C:10]([C:8]([N:5]4[CH2:4][CH2:3][O:44][CH2:7][CH2:6]4)=[O:9])[NH:28][C:13]3=[N:14][CH:15]=2)[CH2:20][CH2:21]1)([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 16727356(4,4-Difluoro-piperidin-1-yl)-[5-(1-isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]-methanone2×

Product 1

HCID 16727359[5-(1-Isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]-morpholin-4-yl-methanoneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 9, intermediate a), from (1-isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid hydrochloride (example 13, intermediate b)), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, morpholine and N,N-diisopropylethylamine (7 eq.) in DMF to give the desired product as a yellow solid (70%).

Sources & evidence

ORD record
ord-c76a00d4c6ec4074965edb6a67b7308e
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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