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

HRID 562735노트

반응식

HRID 562735 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eb37c78e92204fd193633cca21c0c6f0
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067426B2

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