Aluminium lithium hydride → 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropan-1-amine

HRID 218168Notes

Reaction equation

HRID 218168 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:23]([CH3:28])([CH3:27])[C:24]([NH2:26])=O)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:23]([CH3:28])([CH3:27])[CH2:24][NH2:26])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 592511432-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanamide

Product 1

HCID 687048652-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(h)(i) 2-(4-(1-(4-Fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanamide (23 mg, 0.06 mmol) in 3 mL THF was treated with LiAlH4 (0.2 mL of 1.0 M solution in THF) and stirred for 18 h. The reaction was quenched with EtOAc, TFA was added, and the reaction was purified by HPLC to give 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropan-1-amine. (M+H)+=368. This material was coupled to 3,3,3-trifluoropropionic acid using General Coupling Method A. After 16 h, the reaction was purified by HPLC to give 6 mg of 3,3,3-trifluoro-N-(2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropyl)propanamide. (M+H)+=478.

Workup

  1. customThe reaction was quenched with EtOAc, TFA
  2. additionwas added
  3. customthe reaction was purified by HPLC

Sources & evidence

ORD record
ord-8cef1f7e9da14accab81f0da7cc74f97
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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