Sodium Hydroxide → Sodium 5-(4-{1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}phenyl)tetrazol-2-ide

HRID 870064Notes

Reaction equation

HRID 870064 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:35])=[C:5]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[C:6]=1[C:7]([NH:9][C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:20]=[N:21][NH:22][N:23]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].[OH-].[Na+:37]>CCO>[CH3:1][C:2]1[S:3][C:4]([CH3:35])=[C:5]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=2)[C:6]=1[C:7]([NH:9][C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:20]=[N:21][N-:22][N:23]=3)=[CH:15][CH:14]=2)[CH2:11][CH2:12]1)=[O:8].[Na+:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 249529282,5-Dimethyl-N-{1-[4-(2H-tetrazol-5-yl)phenyl]cyclopropyl}-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxamide

Product 1

HCID 24953973Sodium 5-(4-{1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]cyclopropyl}phenyl)tetrazol-2-ide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2,5-dimethyl-N-{1-[4-(2H-tetrazol-5-yl)phenyl]cyclopropyl}-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxamide from Example 14, Step 3 (150 mg, 0.301 mmol) in EtOH (3 mL), was treated with NaOH (1.0N in water, 301 μL, 0.301 mmol). The solution then obtained was concentrated to dryness. Water (20 mL) was added to the residue. The turbid solution was frozen in a bath of dry ice and acetone and lyophilized to afford the desired product as an off-white fluffy solid. MS (−APCI): m/z 496 (M−23)−.

Workup

  1. customThe solution then obtained
  2. concentrationwas concentrated to dryness
  3. additionWater (20 mL) was added to the residue
  4. temperatureThe turbid solution was frozen in a bath of dry ice and acetone

Sources & evidence

ORD record
ord-4e69e387c7b644fc8251835c1433bd72
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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