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

HRID 410195Notes

Reaction equation

HRID 410195 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-9e728b39278f463ca8e044de327f5f97
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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