Aluminium lithium hydride → HCID 178523755, compound

HRID 75503Notes

Reaction equation

HRID 75503 reaction equation
[Cl:1][C:2]1[C:3]([C:28](OCC)=[O:29])=[N:4][N:5]([CH2:7][C@H:8]2[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:27])[C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=3[Cl:26])[CH2:10][CH2:9]2)[CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:26][C:17]1[CH:18]=[CH:19][C:20]([C:22]([F:23])([F:25])[F:24])=[CH:21][C:16]=1[C:15]([NH:14][C@H:11]1[CH2:12][CH2:13][C@H:8]([CH2:7][N:5]2[CH:6]=[C:2]([Cl:1])[C:3]([CH2:28][OH:29])=[N:4]2)[CH2:9][CH2:10]1)=[O:27]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178470465HCID 178470465, compound

Product 1

HCID 178523755HCID 178523755, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of ethyl 4-chloro-1-((trans-4-(2-chloro-5-(trifluoromethyl)benzamido)cyclohexyl)methyl)-1H-pyrazole-3-carboxylate (step 1)(40 mg, 0.081 mmol) in THF (1 ml) was treated with LiAlH4 (6.1 mg, 0.162 mmol) and stirred at 0° C. After 3 h a grey suspension formed. The reaction was quenched by dropwise addition water (0.1 ml in THF 5 ml), followed by 1 M NaOH (0.1 ml) and water (0.3 ml). The reaction mixture was stirred and allowed to warm to RT overnight. The resulting mixture was filtered and the filtrate was concentrated in vacuo. The crude product was triturated with Et2O to afford the title compound as a white solid; 1H NMR (400 MHz, DMSO-d6) δ 8.5 (1H, d), 7.9 (1H, s), 7.8 (1H, d), 7.7 (2H, d), 5.0 (1H, s), 4.4 (2H, s), 3.9 (2H, d), 3.7 (1H, m), 1.9 (2H, d), 1.7 (1H, m), 1.6 (2H, d), 1.2 (2H, m), 1.1 (2H, m). LC-MS: Rt 2.47 mins; MS m/z 450.5 [M+H]+; Method LowpH_v002.

Workup

  1. customAfter 3 h a grey suspension formed
  2. customThe reaction was quenched by dropwise addition water (0.1 ml in THF 5 ml)
  3. stirringThe reaction mixture was stirred
  4. temperatureto warm to RT overnight
  5. filtrationThe resulting mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was triturated with Et2O

Sources & evidence

ORD record
ord-abfceb6738b14b3b9a8650872dcda44f
Source dataset
uspto-grants-2014_09
Patent number
US08835444B2

Reaction notes

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