Trifluoroacetic acid → N-(4-(3-(1,2,3,6-Tetrahydropyridin-4-YL)pyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

HRID 1880062Notes

Reaction equation

HRID 1880062 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:36]=[CH:35][C:14]([O:15][C:16]2[C:21]([C:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH:23]=3)=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:13][CH:12]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:25]1[CH2:24][CH:23]=[C:22]([C:21]2[C:16]([O:15][C:14]3[CH:35]=[CH:36][C:11]([NH:10][C:2]4[S:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)=[CH:12][CH:13]=3)=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59327027tert-butyl 4-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 59326929N-(4-(3-(1,2,3,6-Tetrahydropyridin-4-YL)pyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (501.9 mg) was taken up in DCM and TFA was added. Upon completion, the solvent was evaporated. The residue was taken up in DCM and loaded onto an Agilent SCX cartridge. The impurities were washed from the cartridge with DCM and MeOH. N-(4-(3-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine was filtered from cartridge using 2.0M ammonia in MeOH. MS (ESI, pos. ion) m/z: 401.0 (M+1). IC50 (uM) +++++.

Workup

  1. customUpon completion, the solvent was evaporated
  2. washThe impurities were washed from the cartridge with DCM and MeOH
  3. filtrationN-(4-(3-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine was filtered from cartridge

Sources & evidence

ORD record
ord-2e7eac91230b4d718ed9e9c2d3a5fba3
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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