Water → HCID 57585159, compound

HRID 2077611Notes

Reaction equation

HRID 2077611 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:21]=[CH:20][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:19])[CH3:18])[S:15][C:11]=3[CH:10]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:30]1[CH:31]=[C:32]([NH:37][S:38]([N:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]2)(=[O:40])=[O:39])[C:33]([Cl:36])=[N:34][CH:35]=1.O>C1COCC1>[Cl:36][C:33]1[N:34]=[CH:35][C:30]([C:9]2[CH:21]=[CH:20][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:19])[CH3:18])[S:15][C:11]=3[CH:10]=2)=[CH:31][C:32]=1[NH:37][S:38]([N:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamideHCID 77231507HCID 77231507, compound

Product 1

HCID 57585159HCID 57585159, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a microwave vial equipped with a stirbar and charged with N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.16 g, 0.51 mmol), cesium carbonate (0.41 g, 1.3 mmol), Pd Cl2 (dppf)-DCM (0.062 g, 0.076 mmol), N-(5-bromo-2-chloropyridin-3-yl)piperidine-1-sulfonamide (0.150 g, 0.42 mmol) in THF (3 ml) was added water (0.5 ml). The vial was capped and placed into CEM Microwave for 10 minutes at 100° C., while 100 watts of energy was supplied via Powermax® (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed desired material in the mixture. The organic layer was extracted from the microwave vial by pipet and then diluted the organic with acetonitrile (15 ml) and TFA (0.1 ml). The crude was purified by reverse-phase HPLC. The fractions with desired product were combined and concentrated. The crude was recrystallized from 5:1 EtOAc/Methanol and Hexanes to give N-(6-(6-chloro-5-(piperidine-1-sulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.025 g, 13% yield) as a tan crystalline solid. MS (ESI pos. ion) m/z: 466 (MH+). Calc'd exact mass for C19H20ClN5O3S2: 465. 1H NMR (400 MHz, DMSO-d6): 1.39 (s, 2H), 1.47 (s, 3H), 1.65 (s, 4H), 2.14 (s, 3H), 2.93 (s, 3H), 7.51 (s, 1H), 7.69 (s, 11H), 7.74 (s, 1H), 7.90 (s, 1H), 8.02 (s, 1H).

Workup

  1. customTo a microwave vial equipped with a stirbar
  2. customThe vial was capped
  3. temperaturewas supplied via Powermax® (Simultaneous heating while cooling technology)
  4. extractionThe organic layer was extracted from the microwave vial by pipet
  5. additiondiluted the organic with acetonitrile (15 ml) and TFA (0.1 ml)
  6. customThe crude was purified by reverse-phase HPLC
  7. concentrationconcentrated
  8. customThe crude was recrystallized from 5:1 EtOAc/Methanol and Hexanes

Sources & evidence

ORD record
ord-d0dad8778fc54b4d8459c9374ce63a87
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

Loading…