4-Methylmorpholine → HCID 68587925, compound

HRID 2070892Notes

Reaction equation

HRID 2070892 reaction equation
[C:1]1([C:7]2[N:12]3[N:13]=[C:14]([NH:16][C:17]4[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=4)[N:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:26][CH:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C)C=O.O>[C:1]1([C:7]2[N:12]3[N:13]=[C:14]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:21]([NH:26][CH:27]5[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]5)=[O:22])=[CH:24][CH:25]=4)[N:15]=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 12682914-Amino-1-Boc-piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68587964HCID 68587964, compound

Product 1

HCID 68587925HCID 68587925, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 4-(4-(5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzamido) piperidine-1-carboxylate. A mixture of 4-(5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoic acid (200 mg, 0.6 mmol), tert-butyl 4-aminopiperidine-1-carboxylate (121 mg, 0.6 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (460 mg, 1.2 mmol) and N-methylmorpholine (306 mg, 3.0 mmol) in N,N-dimethylformamide (2 mL) was stirred at room temperature overnight. Water (5 mL) was added, and the precipitate was collected by filtration and washed with water to give tert-butyl 4-(4-(5-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzamido)piperidine-1-carboxylate (220 mg, 72% yield) as a solid. MS (ESI): m/z 535.1 [M+23]+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-4c543e8b13a346c09c5a05918ddf33de
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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