Piperidine → HCID 178423278, 화합물

HRID 635724

반응식

HRID 635724 반응식
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:11]([N:13]1[CH2:17][CH2:16]CC1)=[CH2:12].C(C1C=C2C(=CC=1)CCCC2)(=O)C.N1CCCC1.[CH3:36][C:37]1[N:42]=C(Cl)C([N+]([O-])=O)=[C:39](Cl)[N:38]=1.C([N:51]([CH2:55][CH3:56])[CH:52]([CH3:54])[CH3:53])(C)C.N1CCCCC1.Cl[Sn]Cl>CN(C=O)C.Cl[Ti](Cl)(Cl)Cl.CCN(CC)CC>[CH3:54][CH:52]1[CH2:53][CH:36]([C:37]2[NH:42][C:16]3=[CH:12][C:11]([C:2]4[CH:3]=[CH:4][C:5]5[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=5[CH:1]=4)=[N:13][C:17]3=[CH:39][N:38]=2)[CH2:56][CH2:55][NH:51]1

참가 물질

11

반응물 7

HCID 8082PiperidineHCID 24479Stannous Chloride2회HCID 31268PyrrolidineHCID 698856-AcetyltetralinHCID 81531DiisopropylethylamineHCID 831924,6-Dichloro-2-methyl-5-nitropyrimidineHCID 69561083(1-(2-5,6,7,8-Tetrahydronaphthyl)vinyl)pyrrolidine

생성물 1

HCID 178423278HCID 178423278, 화합물수율 33%

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

Using the method described in Example 30 by employing ((1-(2-5,6,7,8-tetrahydronaphthyl)vinyl) pyrrolidine (freshly prepared before use from 6-acetyltetralin (Lancaster Chemical Company), pyrrolidine and TiCl4 (1.37 g, 6.03 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.20 g, 6.03 mmol), N,N-diisopropylethylamine (1.0 mL, 6.03 mmol), piperidine (1.0 mL, 9.6 mmol), NEt3 (1.0 mL) and SnCl2 (18 mL of a 2 M soln in DMF). In this example the reaction mixture was stirred at room temperature for 48 h after the addition of 2 M SnCl2. The residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant to give 692 mg (33%) of 2-methyl-4-piperidyl-6-(2-5,6,7,8-tetrahydronaphthyl) pyrrolo[3,2-d]pyrimidine as a white-colored solid. This material (692 mg, 2.00 mmol) was dissolved in 5:1 EtOAc/MeOH (40 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (2.00 mL, 2.00 mmol). The solution was left to cool to room temperature. The resulting crystals were collected by filtration, washed with EtOAc (2×10 mL), Et2O (3×15 mL) and dried under vacuum at 60° C. to give 563 mg (24%) of the title compound as a faint yellow colored solid. Mp: 175-177° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.71 (br s, 6), 1.78 (m, 4), 2.57 (s, 3), 2.82 (d, 4, J=16.0), 4.06 (br s, 4), 6.93 (s, 1), 7.23 (d, 1, J=8.6), 7.65-7.67 (m, 2), 11.92 (s, 1), 14.45 (s, 1). MS m/z: 347 (M+1 for free base). Anal. Calcd for C22H26N4.HCl.2.0H2O: C, 63.02; H, 7.40; N, 13.37; Cl, 8.35. Found: C, 63.18; H, 7.43; N, 13.41; Cl, 8.62.

후처리

  1. customwas stirred at room temperature for 48 h
  2. customThe residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant

출처 및 근거

ORD 기록
ord-2eb29f34945e470fae83f5689eeab5fb
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187777B1

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