Trifluoroacetic acid → 5-(3-Aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine

HRID 1926345Notes

Reaction equation

HRID 1926345 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]#[C:10][C:11]1[CH:12]=[N:13][C:14]([NH2:26])=[C:15]([C:17]2[S:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[CH:16]=1)(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][CH2:8][C:9]#[C:10][C:11]1[CH:16]=[C:15]([C:17]2[S:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[C:14]([NH2:26])=[N:13][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67521406HCID 67521406, compound

Product 1

HCID 675208705-(3-Aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-prop-2-ynyl]-carbamic acid tert-butyl ester (0.225 g, 0.6 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (0.5 mL, 6 mmol), the mixture was stirred at RT for 2 h. Aq. satd. NaHCO3 (20 mL) was added, and the mixture was extracted with CH2Cl2/MeOH (10%, 4×30 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated at reduced pressure to give the title compound. 1H NMR (CDCl3, 300 MHz): δ=3.78 (s, 2H), 7.42-7.58 (m, 2H), 7.88 (d, J=6.8 Hz, 1H), 8.05-8.07 (m, 2H), 8.32 (d, J=1.8 Hz, 1H). MS (ES+): m/z=281.14 (100) [MH+]. HPLC: tR=2.01 min (ZQ2, polar—5 min).

Workup

  1. extractionthe mixture was extracted with CH2Cl2/MeOH (10%, 4×30 mL)
  2. dry with materialThe organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-564211c2d0ac4b0d8f56654898eb073e
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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