Hydrochloric Acid → HCID 24803405, compound

HRID 1698068Notes

Reaction equation

HRID 1698068 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[S:21][C:22]4[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][C:23]=4[N:24]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.Cl>C(Cl)Cl>[N:11]1([C:14]2[N:15]=[CH:16][C:17]([C:20]3[S:21][C:22]4[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][C:23]=4[N:24]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 57553404HCID 57553404, compound

Product 1

HCID 24803405HCID 24803405, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[5-(6-Amino-benzothiazol-2-yl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (13 mg, 0.032 mmol) was dissolved in DCM (1 mL), followed by addition of TFA (70 μL). The r.m. was thereafter stirred for 4 hrs at r.t. After addition of HCl (1 M; 1 mL), the two layers were separated. The organic layer was extracted with HCl (1M). The combined aqueous layers were made basic (pH 9-10) with NaOH (2 M) and extracted with DCM. The combined organic layers were washed with brine, dried (Na2SO4), filtered and the solvent was evaporated to give the title compound (10 mg) as an opac colored solid. 1H NMR δ 8.70 (d, 1H) 8.07 (dd, 1H) 7.67 (d, 1H) 7.13 (d, 1H) 6.97 (d, 1H) 6.81 (dd, 1H) 5.45 (s, 2H) 3.53-3.66 (m, 4H) 2.77-2.92 (m, 4H); MS m/z (M+H) 311.

Workup

  1. customthe two layers were separated
  2. extractionThe organic layer was extracted with HCl (1M)
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-428bf9f04c864d0aade05ab7a20e0e53
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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