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Formaldehyde → HCID 67818815、化合物

HRID 1054553
ノート
印刷プレビュー

反応式

HRID 1054553 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 67818137HCID 67818137、化合物

生成物 1

HCID 67818815HCID 67818815、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-608e19ded3a84de0883f4e81a4470d97
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394310B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート