Sodium Hydroxide → HCID 11566711, compound

HRID 1260624Notes

Reaction equation

HRID 1260624 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:29])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[C:8]=1[CH2:27][CH3:28]>C1COCC1.CO>[CH2:27]([C:8]1[N:9]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=2)[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:15]2[C:7]=1[CH2:6][C:5]([OH:29])=[O:4])[CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67219240HCID 67219240, compound

Product 1

HCID 11566711HCID 11566711, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

0.5 M Aqueous NaOH (1.0 ml) is added to a solution of [2-ethyl-1-(4-trifluoromethyl-benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (48 mg, 0.13 mmol) in 1:1 THF/MeOH (1 ml). After 3 hours the reaction is concentrated in vacuo, and the residue dissolved in water. The aqueous solution is cooled in an ice-bath and acidified to pH 2 using concentrated HCl. The resulting precipitate is filtered and dried under high vacuum at 50° C. to yield the titled compound as a white powder. (MH+ 363)

Workup

  1. concentrationAfter 3 hours the reaction is concentrated in vacuo
  2. dissolutionthe residue dissolved in water
  3. temperatureThe aqueous solution is cooled in an ice-bath
  4. filtrationThe resulting precipitate is filtered
  5. customdried under high vacuum at 50° C.

Sources & evidence

ORD record
ord-74d6c5748c574c57828896b7d2940139
Source dataset
uspto-grants-2013_06
Patent number
US08470848B2

Reaction notes

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