Sodium Hydroxide → HCID 136057256, compound

HRID 2252008Notes

Reaction equation

HRID 2252008 reaction equation
Cl.[NH2:2][OH:3].[F:4][C:5]([F:44])([F:43])[C:6]1[CH:7]=[C:8]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[N:22]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:23]([CH:26]=O)=[N:24][N:25]=2)[N:12]=[N:11]1.[OH-].[Na+]>ClCCCl>[F:4][C:5]([F:44])([F:43])[C:6]1[CH:7]=[C:8]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[N:22]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:23]([CH:26]=[N:2][OH:3])=[N:24][N:25]=2)[N:12]=[N:11]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 59644544HCID 59644544, compound

Product 1

HCID 136057256HCID 136057256, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Add hydroxylamine hydrochloride (7 mg) to a 0° C. solution 5-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-4-(2-chloro-benzyl)-4H-[1,2,4]triazole-3-carbaldehyde (50 mg) in 1,2-dichloroethane (1 mL). Stir 60 hours while allowing reaction to slowly warm to RT. Quench reaction by slowly adding 1 N NaOH (1 mL). Extract with CH2Cl2 (2×2 mL) and dry. Purification via silica gel chromatography using 3:1 to 1:1 hexanes:EtOAc gradient gives the desired product (18 mg, 35%). MS (IS) 606.1 (M+1); Rf=0.52 (1:1 hexanes:EtOAc).

Workup

  1. customreaction
  2. customQuench
  3. customreaction
  4. extractionExtract with CH2Cl2 (2×2 mL)
  5. customdry
  6. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-c44fb348b526438e99f948417aa17201
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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