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Hydrochloric Acid → HCID 59471935, 화합물

HRID 2204863
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HRID 2204863 반응식
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:17]3[C:22]([NH2:23])=[N:21][CH:20]=[C:19]([C:24]4[CH:29]=[CH:28][C:27]([C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[CH:26][CH:25]=4)[N:18]=3)=[N:15][N:16]=2)=[CH:8][CH:7]=1)(=O)C.[OH-].[Na+].Cl>CO>[NH2:23][C:22]1[N:21]=[CH:20][C:19]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([N:31]([CH3:33])[CH3:32])=[O:34])=[CH:26][CH:25]=2)=[N:18][C:17]=1[C:14]1[O:13][C:12]([C:9]2[CH:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:11][CH:10]=2)=[N:16][N:15]=1
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참가 물질

5

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HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59471775[4-[5-[3-Amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl acetate

생성물 1

HCID 59471935HCID 59471935, 화합물수율 71.7%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
55 °C

실험 절차

[4-[5-[3-amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl acetate (118 mg, 0.2445 mmol) was suspended in methanol (2 mL) and treated with NaOH (489.0 μL of 1 M, 0.4890 mmol). The resulting mixture was stirred at 55° C. for 1 h. The reaction mixture was cooled to room temperature and then neutralised with HCl (978.0 μL of 1 M, 0.9780 mmol), filtered and washed with acetonitrile. The resulting yellow powder was heated in acetonitrile (5 mL), cooled and filtered to give a pale yellow powder. This was purified by column chromatography on silica gel eluting with 5% MeOH/CH2Cl2 to give the product as a pale yellow powder (73 mg, 70%); 1H NMR (400 MHz, DMSO) d 2.98-3.02 (m, 6H), 4.64 (d, 2H), 5.44 (t, 1H), 7.54-7.62 (dd, 4H), 7.78 (br s, 2H), 8.12-8.18 (dd, 4H) and 8.98 (s, 1H) ppm; MS (ES+) 417.23

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with acetonitrile
  4. temperatureThe resulting yellow powder was heated in acetonitrile (5 mL)
  5. temperaturecooled
  6. filtrationfiltered
  7. customto give a pale yellow powder
  8. customThis was purified by column chromatography on silica gel eluting with 5% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-9177d2ddc48a44b9adb500a7e39309db
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365557B2

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