Piperidine → 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-6-(piperidine-1-carbonyl)-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one

HRID 600436노트

반응식

HRID 600436 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][C:15](=[O:25])[N:16]4[CH:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[C:12]([C:26](O)=[O:27])[N:11]=3)[C:6]=2[CH:29]=1.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:18]=[C:17]4[C:13]([NH:14][C:15](=[O:25])[N:16]4[CH:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[C:12]([C:26]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:27])[N:11]=3)[C:6]=2[CH:29]=1

참가 물질

7

반응물 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 576126552-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylic acid

생성물 1

HCID 576127022-(6-fluoro-1H-benzo[d]imidazol-1-yl)-6-(piperidine-1-carbonyl)-9-(tetrahydro-2H-pyran-4-yl)-7H-purin-8(9H)-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylic acid (25 mg, 0.063 mmol) in THF (2 mL) at 0° C. was added piperidine (8 mg, 0.09 mmol) and triethyl amine (0.052 mL, 0.37 mmol), followed by a solution of triphenylphosphine (0.056 mL, 0.18 mmol) in ethyl acetate. The reaction mixture was allowed to reach room temperature and stirred for 24 h. The solvent was evaporated and a saturated solution of sodium bicarbonate was added to the residue. The solid formed was filtered and dried to give the desired compound as a white solid. Yield: 10 mg, 34%. 1H NMR (400 MHz, DMSO-d6) δ, ppm: 11.89 (s, 1H), 8.20 (d, J=8.5 Hz, 1H), 7.82 (dd, J=4.8, 4.8 Hz, 1H), 7.24 (t, J=6.94 Hz, 1H), 4.58 (m, 1H), 4.03 (t, J=2.2 Hz, 2H), 3.68 (m, 2H), 3.68-3.48 (m, 4H), 2.64-2.55 (m, 2H), 1.79 (d, J=11.6 Hz, 2H), 1.66 (m, 4H), 1.55 (m, 2H); LCMS (EI) m/z 466 (MH)+.

후처리

  1. customto reach room temperature
  2. customThe solvent was evaporated
  3. additiona saturated solution of sodium bicarbonate was added to the residue
  4. customThe solid formed
  5. filtrationwas filtered
  6. customdried

출처 및 근거

ORD 기록
ord-f82141b10a134db19576683fb8d9a22b
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902187B2

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