2-Chlorobenzothiazole → N-(4-(5-(Tetrahydro-2H-pyran-4-YL)pyrimidin-4-yloxy)phenyl)benzo[D]thiazol-2-amine

HRID 410322Notes

Reaction equation

HRID 410322 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[O:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:18]([O:23][C:24]3[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=3)=[N:19][CH:20]=[N:21][CH:22]=2)[CH2:13][CH2:12]1>C(O)(C)C>[O:11]1[CH2:12][CH2:13][CH:14]([C:17]2[C:18]([O:23][C:24]3[CH:30]=[CH:29][C:27]([NH:28][C:2]4[S:3][C:4]5[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=5[N:6]=4)=[CH:26][CH:25]=3)=[N:19][CH:20]=[N:21][CH:22]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 119872-ChlorobenzothiazoleHCID 593268884-(5-(Tetrahydro-2H-pyran-4-YL)pyrimidin-4-yloxy)aniline

Product 1

HCID 46214719N-(4-(5-(Tetrahydro-2H-pyran-4-YL)pyrimidin-4-yloxy)phenyl)benzo[D]thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a microwave vial was added 2-chlorobenzo[d]thiazole (68.5 μL, 0.553 mmol) and 4-(5-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-yloxy)aniline (150 mg, 0.553 mmol) with isopropanol (1.1 mL). The reaction was irradiated at 120° C. for 3 h with microwave irradiation. The crude reaction was concentrated under reduced pressure. Preparative HPLC afforded the target compound as a salt. The material was washed with sat. aq. sodium bicarbonate and extracted with dichloromethane before concentrating the combined organics under reduced pressure to a pale yellow oil. MS (ESI, pos. ion) m/z: 405.0 (M+1). IC50 (uM) +++++.

Workup

  1. customThe reaction was irradiated at 120° C. for 3 h with microwave irradiation
  2. customThe crude reaction
  3. concentrationwas concentrated under reduced pressure
  4. customPreparative HPLC afforded the target compound as a salt
  5. washThe material was washed with sat. aq. sodium bicarbonate
  6. extractionextracted with dichloromethane
  7. concentrationbefore concentrating the combined organics under reduced pressure to a pale yellow oil

Sources & evidence

ORD record
ord-6d005d84b6164a4eac67b168ff2fb8c9
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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