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Potassium Carbonate → MK-8189

HRID 2175405
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HRID 2175405 반응식
[CH3:1][C:2]1[S:6][C:5]([CH2:7][N:8]([C:16]2[CH:21]=[C:20]([O:22][CH2:23][C@H:24]3[CH2:26][C@@H:25]3[C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=3)[N:19]=[C:18]([CH3:34])[N:17]=2)C(=O)OC(C)(C)C)=[N:4][N:3]=1.C([O-])([O-])=O.[K+].[K+]>CO.CCOC(C)=O>[CH3:34][C:18]1[N:17]=[C:16]([NH:8][CH2:7][C:5]2[S:6][C:2]([CH3:1])=[N:3][N:4]=2)[CH:21]=[C:20]([O:22][CH2:23][C@H:24]2[CH2:26][C@@H:25]2[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=2)[N:19]=1
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5

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HCID 11430Potassium CarbonateHCID 86729565tert-Butyl ((5-methyl-1,3,4-thiadiazol-2-yl)methyl)(2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyrimidin-4-yl)carbamate

생성물 1

HCID 71271414MK-8189수율 72%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

To a solution of 2-2 (51.0 mg, 0.11 mmol) in MeOH (0.53 mL) was added K2CO3 (17.5 mg, 0.13 mmol). The resulted suspension was stirred at 70° C. for 2 hour. The mixture was diluted with EtOAc, and then extracted with 1N HCl. The aqueous layer was basified with 5N NaOH and extracted with DCM three times. The combined DCM layers were dried over Na2SO4 and concentrated to give 2-3″ as an off white solid (29 mg, 72%). MS (M+H)+: observed=383.1654, calculated=383.1649. 1H NMR (400 MHz, DMSO-d6): δ 8.22 (s, 1H), 7.82 (br t, J=5.0 Hz, 1H), 7.45 (d, J=7.9 Hz, 1H), 7.17 (d, J=7.7 Hz, 1H), 5.64 (s, 1H), 4.76 (d, J=5.0 Hz, 2H), 4.23 (m, 1H), 4.14 (m, 1H), 2.65 (s, 3H), 2.31 (s, 3H), 2.22 (s, 3H), 2.09 (m, 1H), 1.71 (m, 1H), 1.12 (m, 1H), 0.98 (m, 1H)

후처리

  1. extractionextracted with 1N HCl
  2. extractionextracted with DCM three times
  3. dry with materialThe combined DCM layers were dried over Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0fc85cc44ec247d1a5acf0d025f95334
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062059B2

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