Sodium Carbonate → HCID 59326836, compound

HRID 410282Notes

Reaction equation

HRID 410282 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[S:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][C:17]1[CH:38]=[CH:37][C:20]([O:21][C:22]2[C:27]([C@H:28]3[CH2:33][CH2:32][CH2:31][N:30]([C:34](=[O:36])[CH3:35])[CH2:29]3)=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:19][CH:18]=1>C(Cl)Cl>[S:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][C:17]1[CH:38]=[CH:37][C:20]([O:21][C:22]2[C:27]([C@@H:28]3[CH2:33][CH2:32][CH2:31][N:30]([C:34](=[O:36])[CH3:35])[CH2:29]3)=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 59327073HCID 59327073, compound

Product 1

HCID 59326836HCID 59326836, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(benzo[d]thiazol-2-ylamino)phenol (109 mg, 0.450 mmol), NMP (2 mL) and 1-(3-(2-fluoropyridin-3-yl)piperidin-1-yl)ethanone (50 mg, 0.225 mmol) was added cesium carbonate (147 mg, 0.450 mmol). The reaction mixture was stirred and heated in a Biotage Initiator at 160° C. for 60 minutes. LC-MS shows complete conversion. The reaction was filtered through a Acrodisc syringe filter 0.2 mm ultipor nylon membrane. The filtrate was purified by reverse-phase preparative HPLC (Shimadzu) on a Phenomenex Gemini column (5 micron, C18, 110 Å, Axia, 100×50 mm) eluting at 90 mL/min with an linear gradient of 10% to 80% MeCN (0.1% TFA) in water (0.1% TFA) over 20 minutes to give the product as a TFA salt. The desired fractions were poured into 10% Na2CO3 (aq)/DCM, and the DCM layer separated, dried over MgSO4, and concentrated in vacuo to give a mixture of (S)-1-(3-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)piperidin-1-yl)ethanone (13.5 mg, 0.030 mmol, 27.0% yield) and (R)-1-(3-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)piperidin-1-yl)ethanone (13.5 mg, 0.030 mmol) as a off white solid. MS (ESI, pos. ion) m/z: 445.1 (M+1). IC50 (uM) +++++.

Workup

  1. customthe DCM layer separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give

Sources & evidence

ORD record
ord-bed8c819c8a14b23826f44d0193beca0
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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