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Formaldehyde → HCID 67818815, 화합물

HRID 1054553
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HRID 1054553 반응식
[Cl:1][C:2]1[C:47]([Cl:48])=[CH:46][C:5]2[N:6]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][C@@H:15]3[C@H:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@H:18]4[C@H:17]([N:25]4[C:29]5[N:30]=[CH:31][N:32]=[C:33]([NH:34][CH:35]6[CH2:37][CH2:36]6)[C:28]=5[CH:27]=[CH:26]4)[CH2:16]3)=[N:8][C:4]=2[CH:3]=1.CO.C=O.[BH3-][C:54]#N.[Na+]>C1COCC1>[Cl:1][C:2]1[C:47]([Cl:48])=[CH:46][C:5]2[N:6]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:44])[CH3:45])[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:14][C@@H:15]3[C@H:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@H:18]4[C@H:17]([N:25]4[C:29]5[N:30]=[CH:31][N:32]=[C:33]([NH:34][CH:35]6[CH2:36][CH2:37]6)[C:28]=5[CH:27]=[CH:26]4)[CH2:16]3)[CH3:54])=[N:8][C:4]=2[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 67818137HCID 67818137, 화합물

생성물 1

HCID 67818815HCID 67818815, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

7-[(3aS,4R,6R,6aR)-6-({[4-(5,6-Dichloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl)butyl]amino}methyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-N-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.222 g, 0.311 mmol) was dissolved in THF (5 ml) and MeOH (5 ml) and formaldehyde (0.05 ml, 0.621 mmol) was added at r.t. under N2. NaBH3CN (0.023 g, 0.373 mmol) was added at r.t. and the reaction left for 2 hrs. After this time LCMS analysis showed the reaction was complete so the reaction was quenched by addition of sat. NaHCO3 solution (10 ml), water (10 ml) and DCM (10 ml). The organic layer was separated and the aqueous layer was extracted with DCM (2×10 ml). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product. The crude product was purified by silica flash column chromatography using between 100% DCM and 15% MeOH:95% DCM as eluent to give the product as a colorless oil

후처리

  1. customwas quenched by addition of sat. NaHCO3 solution (10 ml), water (10 ml) and DCM (10 ml)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (2×10 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customThe crude product was purified by silica flash column chromatography

출처 및 근거

ORD 기록
ord-608e19ded3a84de0883f4e81a4470d97
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394310B2

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