Sodium Bicarbonate → HCID 59589715, compound

HRID 1971538Notes

Reaction equation

HRID 1971538 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:25]4[N:26]=[C:27]([NH:29][C:30]([CH:32]5[CH2:34][CH2:33]5)=[O:31])[N:28]=[C:24]4[CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[N:25]4[N:26]=[C:27]([NH:29][C:30]([CH:32]5[CH2:33][CH2:34]5)=[O:31])[N:28]=[C:24]4[CH:23]=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59589819HCID 59589819, compound

Product 1

HCID 59589715HCID 59589715, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-{4-[2-(cyclopropanecarbonyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (0.042 g, 0.091 mmol) in trifluoroacetic acid (2 mL) was stirred for 2 h. Saturated sodium hydrogen carbonate was then added and the mixture was extracted with ethyl acetate and dried over magnesium sulfate. After filtration and concentration under reduced pressure the crude product was purified by preparatory HPLC. LCMS method: 2, RT: 1.97 min; MI: 363 [M+1]. NMR 1H (DMSO) 0.79-0.82 (m, 4H), 1.05 (s, 1H), 2.01 (brs, 1H), 3.10-3.16 (m, 4H), 3.38-3.43 (m, 4H), 7.10 (d, 2H), 7.24 (dd, 1H), 7.58 (dd, 1H), 7.65 (t, 1H), 7.99 (d, 2H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration and concentration under reduced pressure the crude product
  4. customwas purified by preparatory HPLC

Sources & evidence

ORD record
ord-6432dbfbb2814de1a25ba152d49048b9
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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