Triethylamine → HCID 22475355, 화합물

HRID 1060231노트

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HRID 1060231 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[CH2:27][CH:28]=C.F[P-](F)(F)(F)(F)F.N1([O:46][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.Cl.[NH2:66][C:67]1[CH:72]=[CH:71][C:70]([CH2:73][NH2:74])=[C:69]([CH3:75])[N:68]=1>CN(C=O)C.C(Cl)Cl>[NH2:66][C:67]1[N:68]=[C:69]([CH3:75])[C:70]([CH2:73][NH:74][C:28](=[O:46])[CH2:27][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[C:5]([NH:8][S:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=3)(=[O:11])=[O:10])[C:4]=2[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:71][CH:72]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22475359[4-Methyl-2-(phenylmethoxy)-3-prop-2-enylphenyl][(3-methylphenyl)sulfonyl]amineHCID 665242322-Amino-5-aminomethyl-6-methylpyridine dihydrochloride

생성물 1

HCID 22475355HCID 22475355, 화합물수율 100.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

The product of Example 9, step 7 (0.18 g, 0.42 mmol), BOP (0.21 g, 0.47 mmol), triethylamine (0.25 mL, 1.80 mmol), and 2-amino-5-aminomethyl-6-methylpyridine dihydrochloride (Sanderson, P. E., et al. WO 97/01338 (1997)) (0.10 g, 0.48 mmol), were dissolved in DMF (10 mL) and stirred at ambient temperature for 2 hours. The reaction was concentrated in vacuo and the crude product purified by flash column chromatography (gradient elution: 10% to 15% methanol in DCM) giving an impure product that was dissolved in DCM, washed with saturated sodium bicarbonate, water, and brine, dried over sodium sulfate, and filtered. The evaporated filtrate then gave the title compound as a pale yellow solid (0.23 g, 99%). 1H NMR (300 MHz, CDCl3) δ 7.64 (m, 1H), 7.56 (m, 1H), 7.35 (m, 1OH), 7.11 (d, 1H, J=8.3 Hz), 6.94 (d, 1H, J=8.5 Hz), 6.22 (d, 1H, J=8.1 Hz), 5.60 (br t, 1H, J=5.3 Hz), 4.49 (s, 2H), 4.37 (br s, 2H), 4.19 (d, 2H, J=5.5 Hz), 3.56 (s, 2H), 2.34 (s, 3H), 2.23 (s, 3H), 2.22 (s, 3H). Mass spectrum (LCMS, ESI pos.) calc'd. for C30H32N4O4S: 545.2 (M+H). Found: 545.2.

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe crude product purified by flash column chromatography (gradient elution: 10% to 15% methanol in DCM)
  3. customgiving an impure product that
  4. washwashed with saturated sodium bicarbonate, water, and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-28711e3b454b445bad0190129d83395d
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521663B2

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