Sodium hydride → HCID 51353708, compound

HRID 2077509Notes

Reaction equation

HRID 2077509 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:17]1[N:22]=[C:21]([C:23]2[CH:35]=[CH:34][C:26]3[N:27]=[C:28]([NH:30][C:31](=[O:33])[CH3:32])[S:29][C:25]=3[CH:24]=2)[CH:20]=[CH:19][N:18]=1>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]([C:17]2[N:22]=[C:21]([C:23]3[CH:35]=[CH:34][C:26]4[N:27]=[C:28]([NH:30][C:31](=[O:33])[CH3:32])[S:29][C:25]=4[CH:24]=3)[CH:20]=[CH:19][N:18]=2)[CH3:13])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 24974294-Methoxy-N-methylbenzenesulfonamideHCID 51357685N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 51353708HCID 51353708, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Methoxy-N-methylbenzenesulfonamide (228 mg, 1.13 mmol) was dissolved in DMSO (1.6 mL) and NaH (57.5 mg, 60% in mineral oil, 1.44 mmol) was added and the reaction was stirred under nitrogen at RT. After 1 hour, N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (82.3 mg, 0.270 mmol) was added, and the reaction flask was heated in a preheated oil bath (125° C.) and stirred under nitrogen overnight. The reaction was cooled to RT and filtered through a pad of Celite®(diatomaceous earth). Filtrate was concentrated and the crude material was purified on HPLC (10-95% MeCN/water with 0.1% TFA over 30 minutes) to provide N-(6-(2-(4-methoxy-N-methylphenylsulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide. MS (ESI pos. ion) m/z: 470 (MH+). Calculated exact mass for C21H19N5O4S2: 469. 1H NMR (400 MHz, DMSO-d6): 12.52 (s, 1H), 8.64 (d, J=5.0 Hz, 1H), 8.56 (s, 1H), 8.14 (d, J=8.5 Hz, 1H), 7.99 (d, J=8.5 Hz, 2H), 7.84 (d, J=8.5 Hz, 1H), 7.72 (d, J=5.0 Hz, 1H), 7.10 (d, J=9.0 Hz, 2H), 3.82 (s, 3H), 3.69 (s, 3H), 2.23 (s, 3H).

Workup

  1. temperaturethe reaction flask was heated in a preheated oil bath (125° C.)
  2. stirringstirred under nitrogen overnight
  3. temperatureThe reaction was cooled to RT
  4. filtrationfiltered through a pad of Celite®(diatomaceous earth)
  5. concentrationFiltrate was concentrated
  6. customthe crude material was purified on HPLC (10-95% MeCN/water with 0.1% TFA over 30 minutes)

Sources & evidence

ORD record
ord-a46b8d3199ac45fd84064f2a6075569c
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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