Diethyl Ether → HCID 59251120, compound

HRID 218132Notes

Reaction equation

HRID 218132 reaction equation
[CH3:1][C:2]([CH3:22])([C@H:5]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[N:16]=[CH:15]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]#[N:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[F:34][C:35]([F:41])([F:40])[CH2:36][C:37](O)=[O:38]>C1COCC1>[CH3:1][C:2]([CH3:22])([C@H:5]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:21])[N:16]=[CH:15]2)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][NH:4][C:37](=[O:38])[CH2:36][C:35]([F:41])([F:40])[F:34]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 27779723,3,3-Trifluoropropionic acidHCID 21226445Aluminium lithium hydrideHCID 68706179HCID 68706179, compound

Product 1

HCID 59251120HCID 59251120, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(b)(c) To a stirred solution of (S)-2,2-dimethyl-3-(1-methyl-1H-indazol-5-yl)-3-phenylpropanenitrile (54 mg, 0.193 mmol) in anhydrous THF (10 mL) was added 1.0M lithium aluminum hydride in diethyl ether (0.5 mL, 0.5 mmol) portionwise at RT under nitrogen. After stirring at RT for 3 hr, the mixture was carefully quenched with MeOH, poured into brine, extracted with ethyl acetate (2×100 mL), dried (MgSO4) and concentrated. The crude product was coupled with 3,3,3-trifluoropropanoic acid (29 mg, 0.226 mmol) using General Coupling Method A to give 40 mg (51% yield) of (S)—N-(2,2-dimethyl-3-(1-methyl-1H-indazol-5-yl)-3-phenylpropyl)-3,3,3-trifluoropropanamide. MS found: (M+H)+=404.

Workup

  1. customthe mixture was carefully quenched with MeOH
  2. additionpoured into brine
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-025b5d2fc79047ffa3b9c4aef961080b
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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