Sodium hydride → N-(6-(2-(4-fluoro-N-methylphenylsulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

HRID 2077555Notes

Reaction equation

HRID 2077555 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:16]1[N:21]=[C:20]([C:22]2[CH:34]=[CH:33][C:25]3[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:24]=3[CH:23]=2)[CH:19]=[CH:18][N:17]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:16]2[N:21]=[C:20]([C:22]3[CH:34]=[CH:33][C:25]4[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:24]=4[CH:23]=3)[CH:19]=[CH:18][N:17]=2)[CH3:12])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 24400544-fluoro-N-methylbenzene-1-sulfonamideHCID 51357685N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 57584983N-(6-(2-(4-fluoro-N-methylphenylsulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a microwave vial equipped with a stir bar, was added 4-fluoro-N-methylbenzenesulfonamide (0.23 g, 1.2 mmol) and DMF (3 ml). Then sodium hydride (0.120 g, 4.9 mmol) was added to the mixture and allowed to stir 30 minutes. Then palladium(II) acetate (0.011 g, 0.049 mmol), N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.150 g, 0.49 mmol) and Xantphos (0.010 g) was added to the mixture. The vial was capped and placed into a 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 product peaks. The mixture was added to a round-bottom flask and diluted with hot water (150 ml). The mixture was allowed to stir overnight. The precipitate was collected by filtration and washed with Hexanes (3×50 ml), then finally with ethyl ether (50 ml). The crude was diluted with DMSO (5 ml) and purified by reverse-phase HPLC. This gave N-(6-(2-(4-fluoro-N-methylphenylsulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.030 g, 13% yield) as a light-yellow solid. MS (ESI pos. ion) m/z: 458 (MH+). Calc'd exact mass for C20H16FN5O3S2: 457. 1H NMR (400 MHz, DMSO-d6): 1.97 (s, 3H), 3.69 (s, 3H), 7.36-7.47 (m, 3H), 7.64 (s, 1H), 7.82 (d, J=8.03 Hz, 1H), 8.11 (s, 2H), 8.19 (s, 1H), 8.51 (d, J=3.51 Hz, 1H).

Workup

  1. customTo a microwave vial equipped with a stir bar
  2. customThe vial was capped
  3. waitplaced into a CEM Microwave for 10 minutes at 100° C., while 100 watts of energy
  4. temperaturewas supplied via Powermax® (Simultaneous heating while cooling technology)

Sources & evidence

ORD record
ord-875aa21f845a4e8b8a7d2f3ed1a31c93
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

Loading…