Piperidine → 2-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[5-(1-piperidinyl)pentyl]-9H-purin-6-amine

HRID 527795ノート

反応式

HRID 527795 の反応式
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]([O:16][CH3:17])=[N:14][C:13]2[C:8]1=[N:9][C:10]([O:19][C@@H:20]([CH3:24])[CH2:21][CH2:22][CH3:23])=[N:11][C:12]=2[NH2:18].C(N(CC)CC)C.[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>CN(C=O)C>[CH3:24][C@H:20]([O:19][C:10]1[N:9]=[C:8]2[C:13]([N:14]=[C:15]([O:16][CH3:17])[N:7]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:12]([NH2:18])[N:11]=1)[CH2:21][CH2:22][CH3:23]

参加物

5

反応物 3

HCID 8082PiperidineHCID 8471TriethylamineHCID 59252634(S)-9-(5-chloropentyl)-8-methoxy-2-(pentan-2-yloxy)-9H-purin-6-amine

生成物 1

HCID 592525742-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[5-(1-piperidinyl)pentyl]-9H-purin-6-amine収率 51.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

9-(5-Chloropentyl)-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine (80 mg, 0.225 mmol), triethylamine (0.031 ml, 0.225 mmol) and piperidine (0.045 ml, 0.45 mmol) were suspended in DMF (3 ml) and the mixture heated to 70° C. for 18 hours. The solvent was removed and the residue partitioned between DCM (4 ml) and saturated sodium bicarbonate (4 ml). The aqueous phase was re-extracted with further DCM and the combined organic extracts were concentrated and the residue dissolved in 1:1 MeOH:DMSO (1 ml) and purified by MDAP (Method A). The product-containing fractions were combined and evaporated under a stream of nitrogen to give the title compound (47.2 mg).

後処理

  1. customThe solvent was removed
  2. customthe residue partitioned between DCM (4 ml) and saturated sodium bicarbonate (4 ml)
  3. extractionThe aqueous phase was re-extracted with further DCM
  4. concentrationthe combined organic extracts were concentrated
  5. dissolutionthe residue dissolved in 1:1 MeOH
  6. customDMSO (1 ml) and purified by MDAP (Method A)
  7. customevaporated under a stream of nitrogen

出典と根拠

ORDレコード
ord-1721342fb46c48f7a8bd6b750b4e7cad
出典データセット
uspto-grants-2016_05
特許番号
US09346806B2

反応ノート

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