Pyrrolidine → HCID 16727131, compound

HRID 1437712Notes

Reaction equation

HRID 1437712 reaction equation
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([O:17][CH:18]3[CH2:23][CH2:22][N:21]([CH:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]3)[CH:16]=[C:11]2[CH:10]=[C:9]1[C:27]([O-])=[O:28])=O)(C)(C)C.[Li+].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]=N1.N1CCCC1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:24]([N:21]1[CH2:22][CH2:23][CH:18]([O:17][C:15]2[CH:16]=[C:11]3[CH:10]=[C:9]([C:27]([N:38]4[CH2:39][CH2:44][CH2:43][CH2:42]4)=[O:28])[NH:8][C:12]3=[N:13][CH:14]=2)[CH2:19][CH2:20]1)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68424295HCID 68424295, compound

Product 1

HCID 16727131HCID 16727131, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 9, intermediate a), from lithium 1-tert-butoxycarbonyl-5-(1-isopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate, O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, pyrrolidine and N,N-diisopropylethylamine in DMF to give the desired product as a light yellow solid (33%).

Sources & evidence

ORD record
ord-17b3b393c2e04b159be8303019041b52
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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