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Hexane → 4-(8-Oxo-5-(4-(4-oxobutyl)phenyl)-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-2-(trifluoromethyl)benzonitrile

HRID 1192879
Notes
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Reaction equation

HRID 1192879 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:20](=[S:21])[N:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=3)[C:18](=[O:34])[C:14]32[CH2:17][CH2:16][CH2:15]3)=[CH:9][CH:8]=1.CCCCCC>ClCCl.[H-].C([Al+]CC(C)C)C(C)C>[O:34]=[C:18]1[C:14]2([CH2:17][CH2:16][CH2:15]2)[N:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][CH:3]=[O:2])=[CH:12][CH:11]=2)[C:20](=[S:21])[N:19]1[C:22]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 8058HexaneHCID 866300064-{4-[7-(4-Cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-phenyl}-butyric acid methyl ester

Product 1

HCID 252681274-(8-Oxo-5-(4-(4-oxobutyl)phenyl)-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 21225700
Diisobutylaluminumhydride
Solvent

Conditions

Temperature
21 °C

Procedure

To a stirred solution of 4-{4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-phenyl}-butyric acid methyl ester (67) [ND-4] (61 mg, 0.12 mmol) in dichloromethane (5 mL), 1M diisobutylaluminum hydride (DIBAL) solution in hexane (0.16 mL, 0.16 mmol) was added at −78° C. After 30 min, the reaction mixture was quenched with saturated Rochelle's salt solution. The resulting mixture was stirred at 21° C. until both phases were clearly separated and the organic layer was clear. After extraction, the separated organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The crude mixture of (66) and (68) was purified by flash column chromatography (hexane:ethyl acetate,

Workup

  1. customthe reaction mixture was quenched with saturated Rochelle's salt solution
  2. customwere clearly separated
  3. extractionAfter extraction
  4. dry with materialthe separated organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. additionThe crude mixture of (66) and (68)
  8. customwas purified by flash column chromatography (hexane

Sources & evidence

ORD record
ord-df61238aeb014f8fbb2c29a558018860
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08680291B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes