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Acetyl chloride → HCID 58094900, 화합물

HRID 2282332
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HRID 2282332 반응식
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[S:13][C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH2:23])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:11][C:10]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])[CH:2]=[CH2:3].[C:32](Cl)(=[O:34])[CH3:33]>N1C=CC=CC=1>[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[S:13][C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH:23][C:32](=[O:34])[CH3:33])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:11][C:10]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])[CH:2]=[CH2:3]
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참가 물질

4

반응물 2

HCID 6367Acetyl chloride2회HCID 58095014HCID 58095014, 화합물

생성물 1

HCID 58094900HCID 58094900, 화합물수율 94.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a mixture of 7-[5-(1-allyl-1H-imidazol-2-yl)-4-(2,4-dichlorophenyl)-2-thienyl][1,3]thiazolo[5,4-d]pyrimidin-2-amine (200 mg, 0.41 mmol) and pyridine (20 mL), was added acetyl chloride (0.30 mL, 4.2 mmol) at rt. After being stirred for 1 hour, acetyl chloride (0.30 mL, 4.2 mmol) was added at rt. After being stirred for 2 hours, the mixture was concentrated in vacuo. To the residue, were added sat. NaHCO3 and EtOAc. After being stirred for 30 min, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with ether to yield the title compound (204 mg, 90%) as a pale yellow solid. LCMS: (AA) ES+527, 529. 1H NMR (400 MHz, d6-DMSO) δ: 12.76 (s, 1H), 8.97 (s, 1H), 8.68 (s, 1H), 7.77 (d, J=2.3 Hz, 1H), 7.44 (dd, J=8.3, 2.3 Hz, 1H), 7.26-7.23 (m, 2H), 7.04 (d, J=1.3 Hz, 1H), 5.70-5.62 (m, 1H), 5.09-5.06 (m, 1H), 4.85-4.80 (m, 1H), 4.38 (d, J=5.3 Hz, 2H), 2.25 (s, 3H).

후처리

  1. stirringAfter being stirred for 2 hours
  2. concentrationthe mixture was concentrated in vacuo
  3. additionTo the residue, were added sat. NaHCO3 and EtOAc
  4. stirringAfter being stirred for 30 min
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washThe residue was washed with ether

출처 및 근거

ORD 기록
ord-a380bd73926e4a1fb37e6c8294a36b22
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09139589B2

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