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Tributylphosphine → 4-[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-yloxy]-piperidine-1-carboxylic Acid Tert-Butyl Ester

HRID 1394220
Notes
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Reaction equation

HRID 1394220 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:17][CH3:18])[C:9]3[C:14]([OH:15])=[CH:13][N:12]=[CH:11][C:10]=3[N:16]=2)=[N:4][O:5][N:6]=1.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29](O)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([O:15][C:14]2[C:9]3[N:8]([CH2:17][CH3:18])[C:7]([C:3]4[C:2]([NH2:1])=[N:6][O:5][N:4]=4)=[N:16][C:10]=3[CH:11]=[N:12][CH:13]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 596818032-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-ol

Product 1

HCID 691583674-[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-yloxy]-piperidine-1-carboxylic Acid Tert-Butyl Ester
Yield 18.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from Example 283 (0.1 g, 0.406 mmol), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.074 g, 0.369 mmol) and tributylphosphine (0.074 g, 0.369 mmol) in tetrahydrofuran (5 ml) was treated with 1,1′-(Azodicarbonyl)-dipiperidine (0.093 g, 0.369 mmol) and heated at reflux for 18 hours. The reaction was then cooled to RT and then applied to a SCX ion exchange column and eluted with methanol and then a mixture of methanol/0.880 ammonia (9:1). The basic fractions were then reduced and the solid residue chromatographed on silica gel eluting with ethyl acetate to afford the title compound, (0.03 g, 17%); MS (ES+) m/e 430 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. washeluted with methanol
  4. additiona mixture of methanol/0.880 ammonia (9:1)
  5. customthe solid residue chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-583ab0bea8614428a35ee737c60cf6f6
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07348339B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes