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Hydrazine → tert-butyl 8-(2,2-difluoroethyl)-10-(4-methyl-1H-pyrazol-5-yl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

HRID 712968
Notes
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Reaction equation

HRID 712968 reaction equation
[F:1][CH:2]([F:26])[CH2:3][N:4]1[CH2:21][CH:20]([C:22](=O)[CH2:23][CH3:24])[O:19][C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:5]1.C[N:28]([CH:30](OC)OC)C.[NH2:35]N>CO>[F:26][CH:2]([F:1])[CH2:3][N:4]1[CH2:21][CH:20]([C:22]2[NH:35][N:28]=[CH:30][C:23]=2[CH3:24])[O:19][C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:10][CH2:11]2)[CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9321HydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 86672467Tert-butyl 8-(2,2-difluoroethyl)-10-propanoyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 86672470tert-butyl 8-(2,2-difluoroethyl)-10-(4-methyl-1H-pyrazol-5-yl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylateYield 33.42%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

tert-Butyl 8-(2,2-difluoroethyl)-10-propanoyl-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (225 mg, 0.598 mmol) and DMF-DMA (1.0 mL, 7.53 mmol) were heated in a sealed vial at 105° C. overnight. The reaction mixture was concentrated and then diluted with methanol (1 mL). Hydrazine (60 μL, 1.9 mmol) was added in 3 aliquots every hour over 3 hours and then the reaction mixture was stirred for an additional 1 hour. The reaction mixture was diluted with methanol, microfiltered and purified by preparative LCMS (10-99% ACN/Water, HCl modifier) to give tert-butyl 8-(2,2-difluoroethyl)-10-(4-methyl-1H-pyrazol-5-yl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (80 mg, 0.2 mmol, 33.42%) as a yellow oil. ESI-MS m/z calc. 400.2. found 401.5 (M+1)+; Retention time: 1.36 minutes (3 min run).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with methanol (1 mL)
  3. custommicrofiltered and purified by preparative LCMS (10-99% ACN/Water, HCl modifier)

Sources & evidence

ORD record
ord-3529d86c7efd47109734e8419a357d54
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181273B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes