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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Sulfuric acid magnesium salt (1:1) → 7-[(3aS,4R,6R,6aR)-6-{[({3-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutyl}methyl)(propan-2-yl)amino]methyl}-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2040674
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HRID 2040674 반응식
[C:1]([C:5]1[CH:28]=[CH:27][C:8]2[N:9]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:10]([CH2:12][CH:13]3[CH2:16][CH:15]([CH:17]=O)[CH2:14]3)=[N:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][C:30]1([CH3:53])[O:34][C@@H:33]2[C@@H:35]([CH2:48][NH:49][CH:50]([CH3:52])[CH3:51])[CH2:36][C@@H:37]([N:38]3[C:42]4[N:43]=[CH:44][N:45]=[C:46]([NH2:47])[C:41]=4[CH:40]=[CH:39]3)[C@@H:32]2[O:31]1.S([O-])([O-])(=O)=O.[Mg+2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([C:5]1[CH:28]=[CH:27][C:8]2[N:9]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[C:10]([CH2:12][CH:13]3[CH2:16][CH:15]([CH2:17][N:49]([CH2:48][C@@H:35]4[C@H:33]5[O:34][C:30]([CH3:53])([CH3:29])[O:31][C@H:32]5[C@H:37]([N:38]5[C:42]6[N:43]=[CH:44][N:45]=[C:46]([NH2:47])[C:41]=6[CH:40]=[CH:39]5)[CH2:36]4)[CH:50]([CH3:52])[CH3:51])[CH2:14]3)=[N:11][C:7]=2[CH:6]=1)([CH3:3])([CH3:2])[CH3:4]
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참가 물질

6

반응물 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 5049666Sodium triacetoxyborohydrideHCID 677763337-[(3aS,4R,6R,6aR)-2,2-dimethyl-6-[(propan-2-ylamino)methyl]-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 866661243-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutane-1-carbaldehyde

생성물 1

HCID 67774857
7-[(3aS,4R,6R,6aR)-6-{[({3-[(5-tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutyl}methyl)(propan-2-yl)amino]methyl}-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine
수율 11.5%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

3-[(5-Tert-butyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)methyl]cyclobutane-1-carbaldehyde (282.3 mg, 0.7 mmol), 7-[(3aS,4R,6R,6aR)-2,2-dimethyl-6-[(propan-2-ylamino)methyl]-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (243.41 mg, 0.7 mmol) and magnesium sulfate (127.22 mg, 1.06 mmol) were stirred in 1,2-dichloroethane (10 ml) for 15 mins. Sodium triacetoxyborohydride (179.21 mg, 0.85 mmol) was added, and the reaction stirred overnight. The reaction was quenched by the addition of sat. Na2CO3 (10 ml), and the solution was extracted with DCM (3×10 ml). The combined organics were dried (MgSO4) and concentrated. The crude material was purified by mass directed prep-HPLC (acidic method). After combining the fractions, a small amount of 7M NH3 in MeOH was added to basify the solution. After concentration, the residue was partitioned between water (5 ml) and DCM (5 ml), and the layers separated. The aqueous layer was extracted with DCM (2×3 ml) and the combined organics were dried (MgSO4) and concentrated to afford the title compound (58.7 mg, 11%) as a colourless gum: MS (ESI+) for C41H63N7O3Si m/z 730.2 [M+H]+; LC purity 95% (UV), 100% (ELS), (ret. time, 1.65 min); 1H NMR (500 MHz, CHLOROFORM-d) δH 8.30 (s, 1 H), 7.75 (s, 1 H), 7.32 (s, 2 H), 7.04 (d, J=3.6 Hz, 1 H), 6.37 (d, J=3.6 Hz, 1 H), 5.40-5.50 (m, 2 H), 5.24 (br. s., 2 H), 4.89-5.04 (m, 2 H), 4.45 (d, J=5.2 Hz, 1 H), 3.50 (s, 3 H), 2.11-3.09 (m, 13 H), 2.01 (s, 6 H), 1.34-1.49 (m, 6 H), 1.29 (s, 3 H), 0.85-1.02 (m, 8 H), −0.11-0.05 (m, 9 H).

후처리

  1. customThe reaction was quenched by the addition of sat. Na2CO3 (10 ml)
  2. extractionthe solution was extracted with DCM (3×10 ml)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude material was purified by mass
  6. additiona small amount of 7M NH3 in MeOH was added
  7. concentrationAfter concentration
  8. customthe residue was partitioned between water (5 ml) and DCM (5 ml)
  9. customthe layers separated
  10. extractionThe aqueous layer was extracted with DCM (2×3 ml)
  11. dry with materialthe combined organics were dried (MgSO4)
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-47e6573f7f98465e85fdc06b27e05f5f
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08580762B2

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