Trifluoroacetic acid → 8-(2-chlorophenyl)-9-(4-chlorophenyl)-N-[(3S)-piperidin-3-yl]-9H-purin-6-amine

HRID 715621노트

반응식

HRID 715621 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([NH:17][C@H:18]1[CH2:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]1)[N:13]=[CH:12][N:11]=2.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[C:10]2[C:15]([N:16]=1)=[C:14]([NH:17][C@H:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1)[N:13]=[CH:12][N:11]=2

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 71450192tert-butyl (3S)-3-{[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}piperidine-1-carboxylate

생성물 1

HCID 714573468-(2-chlorophenyl)-9-(4-chlorophenyl)-N-[(3S)-piperidin-3-yl]-9H-purin-6-amine수율 66.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl (3S)-3-{[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]amino}piperidine-1-carboxylate (120 mg, 0.22 mmol) was stirred in dichloromethane (7 mL) and trifluoroacetic acid (3 mL) for 16 h. The reaction was concentrated in vacuo. The crude product was dissolved in ethyl acetate and washed with saturated NaHCO3. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with brine and dried with MgSO4. The crude material was purified by silica gel column chromatography using 0-100% CMA 80/ethyl acetate to yield 64 mg (65%) of 8-(2-chlorophenyl)-9-(4-chlorophenyl)-N-[(3S)-piperidin-3-yl]-9H-purin-6-amine. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.55-1.86 (m, 4 H) 2.01-2.14 (m, 1 H) 2.66-2.85 (m, 2 H) 2.87-3.04 (m, 1 H) 3.32 (dd, J=11.77, 2.35 Hz, 1 H) 4.39 (br. s., 1 H) 6.20 (d, J=5.84 Hz, 1 H) 7.12-7.66 (m, 8 H) 8.47 (s, 1 H), [M+H]+ 439.6.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionThe crude product was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried with MgSO4
  7. customThe crude material was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b0735aeafb834b18af5d3600172e5f9f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187480B2

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