Ammonium Chloride → HCID 86601258, compound

HRID 2252009Notes

Reaction equation

HRID 2252009 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][C:13]=2[Cl:19])[C:9]([C:20]2[N:21]=[N:22][N:23]([CH2:28][C:29]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=3)[C:24]=2[N:25]([CH3:27])[CH3:26])=[N:8][N:7]=1)C.[Li+].[BH4-].[NH4+].[Cl-]>C1COCC1>[F:37][C:35]([F:36])([F:38])[C:33]1[CH:34]=[C:29]([CH:30]=[C:31]([C:39]([F:42])([F:40])[F:41])[CH:32]=1)[CH2:28][N:23]1[C:24]([N:25]([CH3:26])[CH3:27])=[C:20]([C:9]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:6]([CH2:5][CH2:4][OH:3])=[N:7][N:8]=2)[N:21]=[N:22]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 86601259HCID 86601259, compound

Product 1

HCID 86601258HCID 86601258, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve [5-[1-(3,5-bis-trifluoromethyl-benzyl)-5-dimethylamino-1H-[1,2,3]triazol-4-yl]-4-(2-chloro-4-fluoro-benzyl)-4H-[1,2,4]triazol-3-yl]-acetic acid ethyl ester (338 mg) in THF (5 mL). Cool to 0° C., add 2M LiBH4 (0.8 mL, 2M soln in THF) and stir overnight while slowly warming to RT. Pour reaction into aqueous NH4Cl (15 mL) and extract with EtOAc (2×15 mL). Purify via radial chromatography using a gradient of 1:1 to 1:5 hexanes:EtOAc to give the title compound (137 mg, 44%). MS (IS) 592.0 (M+1); Rf=0.11 (1:5 hexanes:EtOAc).

Workup

  1. temperaturewhile slowly warming to RT
  2. additionPour
  3. extractionextract with EtOAc (2×15 mL)
  4. customPurify via radial chromatography

Sources & evidence

ORD record
ord-b3d9ed28fbda4fef8092b548dccbc821
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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