Hydrochloric Acid → HCID 59464253, compound

HRID 1713788Notes

Reaction equation

HRID 1713788 reaction equation
[CH3:1][C:2]1[C:3]([N:26]2[CH2:31][CH2:30][CH:29]([CH:32]([CH3:38])[C:33]([O:35]CC)=[O:34])[CH2:28][CH2:27]2)=[N:4][CH:5]=[C:6]([NH:8][C:9]([C:11]2[O:12][C:13]([NH:16][C:17]3[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=3[F:25])=[N:14][N:15]=2)=[O:10])[CH:7]=1.C[Si](C)(C)[O-].[K+].O.Cl>C1COCC1>[CH3:1][C:2]1[C:3]([N:26]2[CH2:27][CH2:28][CH:29]([CH:32]([CH3:38])[C:33]([OH:35])=[O:34])[CH2:30][CH2:31]2)=[N:4][CH:5]=[C:6]([NH:8][C:9]([C:11]2[O:12][C:13]([NH:16][C:17]3[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=3[F:25])=[N:14][N:15]=2)=[O:10])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23668039Potassium trimethylsilanolate2×HCID 68681904HCID 68681904, compound

Product 1

HCID 59464253HCID 59464253, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 2-(1-{3-methyl-5-[({5-[(2,4,5-trifluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridine-2-yl}piperidin-4-yl)propanoate (Example 692) (70 mg; 0.13 mmol) was dissolved in dry THF (2.0 mL), treated with potassium trimethylsilanolate (167 mg; 1.30 mmol) and placed in a Biotage ‘Initiator’ microwave. The reaction was heated at 90° C. for 35 mins., monitoring by LCMS, as a yellow precipitate formed. The reaction was incomplete (˜9% ester remained). A further portion of potassium trimethylsilanolate (17 mg) was added and the reaction was returned to the microwave for 15 mins. Very little more reaction was seen (ie ˜5% of starting ester remained). The resulting yellow suspension was treated with water (3 mL) and acidified, to about pH 2, with dropwise addition of aq. 1M HCl. With vigorous stirring for ˜15 mins, a white precipitate formed which was filtered, washed with water and dried under vacuum at 60° C. to give the title compound (45 mg; 79% yield).

Workup

  1. customformed
  2. customVery little more reaction
  3. customa white precipitate formed which
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-c6d23d49ee0b46fd86c04ded27b86599
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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