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Sodium Carbonate → HCID 57585103, 화합물

HRID 2077560
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HRID 2077560 반응식
Br[C:2]1[CH:3]=[C:4]([N:8]([CH3:22])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:31]2[CH:43]=[CH:42][C:34]3[N:35]=[C:36]([NH:38][C:39](=[O:41])[CH3:40])[S:37][C:33]=3[CH:32]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd]>[CH3:22][N:8]([C:4]1[CH:3]=[C:2]([C:31]2[CH:43]=[CH:42][C:34]3[N:35]=[C:36]([NH:38][C:39](=[O:41])[CH3:40])[S:37][C:33]=3[CH:32]=2)[CH:7]=[N:6][CH:5]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamideHCID 67097612HCID 67097612, 화합물

생성물 1

HCID 57585103HCID 57585103, 화합물

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 31275
1,4-Dioxane
용매

실험 절차

To a microwave vial equipped with a stir bar was charged with N-(5-bromopyridin-3-yl)-N-methyl-4-(trifluoromethyl)benzenesulfonamide (0.250 g, 0.6 mmol) in 1,4-dioxane (3 ml), was added N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.300 g, 0.9 mmol), Pd FibreCat® (0.024 g, 20%) and 2M sodium carbonate (0.8 ml, 2 mmol). The vial was capped and then placed into a CEM Microwave for 15 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, N-deacylated material and boronic ester in the mixture. The reaction was stopped at this point, to prevent further de-acylation of product. The mixture was diluted with DCM and saturated sodium bicarbonate solution. The organic layer was collected by extracting with DCM (3×20 ml). Combined organic extracts, dried over sodium sulfate, filtered and concentrated in vacuo. The crude was diluted with ethyl acetate and stirred 10 minutes. The precipitate was collected by filtration and washed with 1:1 ethyl acetate/hexanes. This gave N-(6-(5-(N-methyl-4-(trifluoromethyl)phenylsulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.160 g, 50% yield) as a tan crystalline solid. MS (ESI pos. ion) m/z: 507 (MH+). Calc'd exact mass for C22H17F3N4O3S2: 506. 1H NMR (400 MHz, DMSO-d6): 2.23 (s, 3H), 3.31 (s, 3H), 7.71 (d, J=7.53 Hz, 1H), 7.81 (d, J=7.03 Hz, 3H), 7.87 (s, 1H), 8.02 (d, J=6.53 Hz, 2H), 8.26 (s, 1H), 8.42 (s, 1H), 8.91 (s, 1H), 12.44 (s, 1H).

후처리

  1. customTo a microwave vial equipped with a stir bar
  2. customThe vial was capped
  3. temperaturewas supplied via Powermax® (Simultaneous heating while cooling technology)

출처 및 근거

ORD 기록
ord-729ac2ff3e574ddd8a5c7cfd7d989c03
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07928140B2

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