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Ammonium Chloride → 4-[1-(2-aminopyrimidin-4-yl)-2-(oxetan-3-yloxy)-1H-1,3-benzodiazol-6-yl]-2-(pyrimidin-2-yl)but-3-yn-2-ol

HRID 1398686
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HRID 1398686 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([O:11][CH:12]3[CH2:15][O:14][CH2:13]3)[N:8]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[N:17]=3)[C:7]=2[CH:23]=1)#[CH:2].C([N-]C(C)C)(C)C.[Li+].[N:32]1[CH:37]=[CH:36][CH:35]=[N:34][C:33]=1[C:38](=[O:40])[CH3:39].[Cl-].[NH4+]>C1COCC1>[NH2:22][C:18]1[N:17]=[C:16]([N:8]2[C:7]3[CH:23]=[C:3]([C:1]#[C:2][C:38]([C:33]4[N:34]=[CH:35][CH:36]=[CH:37][N:32]=4)([OH:40])[CH3:39])[CH:4]=[CH:5][C:6]=3[N:10]=[C:9]2[O:11][CH:12]2[CH2:13][O:14][CH2:15]2)[CH:21]=[CH:20][N:19]=1
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HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 116079091-(Pyrimidin-2-yl)ethan-1-oneHCID 866696124-[6-ethynyl-2-(oxetan-3-yloxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

생성물 1

HCID 681817484-[1-(2-aminopyrimidin-4-yl)-2-(oxetan-3-yloxy)-1H-1,3-benzodiazol-6-yl]-2-(pyrimidin-2-yl)but-3-yn-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of 4-[6-ethynyl-2-(oxetan-3-yloxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (270 mg, 0.88 mmol) in dry THF (5 mL) at −78° C. was introduced lithium diisopropylamide (1.10 mL of a 2M solution in THF, 2.20 mmol). After 15 minutes, 1-pyrimidin-2-yl-ethanone (107 mg, 0.88 mmol) was added and the reaction mixture maintained at −78° C. for 15 minutes. Following 2 hr at RT, saturated aqueous ammonium chloride (0.5 ml) was added and the solution concentrated in vacuo. The residue was dissolved in DCM (10 mL), washed with water (2 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by column chromatography (Biotage, DCM containing a 0-12% gradient of methanol) furnished the title compound as a yellow solid: 1H NMR (500 MHz, DMSO) delta 1.90 (3H, s), 4.78 (2H, dd, J=7.8, 4.9 Hz), 4.98 (2H, t, J=7.1 Hz), 5.87-5.80 (1H, m), 6.16 (1 H, s), 7.11 (1H, d, J=5.5 Hz), 7.14 (2H, s), 7.25 (1H, dd, J=8.2, 1.2 Hz), 7.45 (1H, d, J=8.2 Hz), 7.52 (1H, t, J=4.8 Hz), 8.16 (1H, s), 8.44 (1H, d, J=5.5 Hz), 8.91 (2H, d, J=4.8 Hz); LC-MS: m/z=+430.05 (M+H)+.

후처리

  1. waitFollowing 2 hr at RT
  2. concentrationthe solution concentrated in vacuo
  3. dissolutionThe residue was dissolved in DCM (10 mL)
  4. washwashed with water (2 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by column chromatography (Biotage, DCM containing a 0-12% gradient of methanol)

출처 및 근거

ORD 기록
ord-97e5158e5a1047079a15c4f8c35795c9
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901313B2

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