N-(4-(3-(3,4-dihydro-2H-pyran-2-yl)pyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine → (+/-)-N-(4-(3-(Tetrahydro-2H-pyran-2-YL)pyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

HRID 1880100Notes

Reaction equation

HRID 1880100 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[C:7]1[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[S:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[N:25]=3)=[CH:16][CH:15]=2)=[N:9][CH:10]=[CH:11][CH:12]=1>[Pd].C(O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[S:22][C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[N:25]=3)=[CH:16][CH:15]=2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 59326996N-(4-(3-(3,4-dihydro-2H-pyran-2-yl)pyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine

Product 1

HCID 59326804(+/-)-N-(4-(3-(Tetrahydro-2H-pyran-2-YL)pyridin-2-yloxy)phenyl)benzo[D]thiazol-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-(4-(3-(3,4-dihydro-2H-pyran-2-yl)pyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine (357 mg, 0.889 mmol) and palladium on carbon, wet (95 mg, 0.089 mmol) in ethanol (0.15M) was placed under an atmosphere of hydrogen (g) and stirred at room temperature. After the starting material was completely consumed, the mixture was filtered through a cake of celite, washed with MeOH & THF and filtrate was concentrated to dryness. The residue was purified by silica gel chromatography to give the desired product as a racemic mixture. MS (ESI, pos. ion) m/z: 404.0 (M+1). IC50 (uM) +++++.

Workup

  1. customAfter the starting material was completely consumed
  2. filtrationthe mixture was filtered through a cake of celite
  3. washwashed with MeOH & THF and filtrate
  4. concentrationwas concentrated to dryness
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c486b186c57e4e1bb5d78b9e393a03e1
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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