Trifluoroacetic acid → 2-(1-(5-Propylpyrimidin-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole

HRID 1429526Notes

Reaction equation

HRID 1429526 reaction equation
[CH2:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[S:18][C:19]4[CH:25]=[C:24]([C:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH:27]=5)[CH:23]=[CH:22][C:20]=4[N:21]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)[CH2:2][CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([O:16][C:17]3[S:18][C:19]4[CH:25]=[C:24]([C:26]5[CH2:31][CH2:30][NH:29][CH2:28][CH:27]=5)[CH:23]=[CH:22][C:20]=4[N:21]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67464591tert-Butyl 4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 674627952-(1-(5-Propylpyrimidin-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazoleYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (166 mg, 0.310 mmol) in CH2Cl2 (3 mL) was added TFA (0.358 mL, 4.65 mmol). Upon completion of addition, the reaction mixture was stirred at rt for 3 hrs. After this time, the reaction mixture was diluted with CH2Cl2 (10 mL) and washed with aq NaOH (1 N, 5 mL) and brine (5 mL) and then dried (Na2SO4). The resulting mixture was filtered and concentrated under reduced pressure to afford Compound 1E as a light yellow solid (124 mg, 0.285 mmol, 92% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 8.17 (2H, s), 7.59-7.68 (2H, m), 7.42 (1H, dd, J=8.5, 1.9 Hz), 6.11-6.21 (1H, m), 5.39-5.55 (1H, m), 4.23 (2H, ddd, J=13.3, 6.8, 3.9 Hz), 3.62-3.77 (2H, m), 3.56 (2H, q, J=2.6 Hz), 3.14 (2H, t, J=5.7 Hz), 2.46-2.55 (2H, m), 2.41 (2H, t, J=7.6 Hz), 2.13-2.24 (2H, m), 1.88-2.00 (2H, m), 1.52-1.61 (3H, m), 0.95 (3H, t, J=7.5 Hz).

Workup

  1. additionUpon completion of addition
  2. washwashed with aq NaOH (1 N, 5 mL) and brine (5 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationThe resulting mixture was filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed343cea60534a77887dc334d6c54afe
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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