Trifluoroacetic acid → HCID 86677065, compound

HRID 1429562Notes

Reaction equation

HRID 1429562 reaction equation
C(C1C=NC(N2CCC(C[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)CC2)=NC=1)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:29]1[CH2:28][CH:27]=[C:26]([C:24]2[CH:23]=[CH:22][C:20]3[N:21]=[CH:17][S:18][C:19]=3[CH:25]=2)[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67467656tert-butyl 4-(2-((1-(5-propylpyrimidin-2-yl)piperidin-4-yl)methyl)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 86677065HCID 86677065, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(2-((1-(5-propylpyrimidin-2-yl)piperidin-4-yl)methyl)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (253 mg, 0.474 mmol) in DCM (4 mL) was added TFA (0.45 mL, 5.7 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with DCM (4 mL), washed with aq NaOH (1 N, 10 mL) and brine. The combined organic layers were dried (Na2SO4), filtered, and concentrated to afford 2-O-(5-propylpyrimidin-2-yl)piperidin-4-yl)methyl)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole (206 mg, 0.451 mmol, 95% yield) as an off white solid. LCMS (m/z)=434 (M+H)+.

Workup

  1. washwashed with aq NaOH (1 N, 10 mL) and brine
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2f1fa5e14e164b2cada49bda3a0c9697
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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