Diisopropylethylamine → HCID 70873752, 화합물

HRID 2208854노트

반응식

HRID 2208854 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:20][CH3:21])[CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[NH2:64][CH2:65][C:66]1[C:67](=[O:74])[NH:68][C:69]([CH3:73])=[CH:70][C:71]=1[CH3:72]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:20][CH3:21])[CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH:64][CH2:65][C:66]1[C:67](=[O:74])[NH:68][C:69]([CH3:73])=[CH:70][C:71]=1[CH3:72])=[O:9]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 70873687HCID 70873687, 화합물

생성물 1

HCID 70873752HCID 70873752, 화합물수율 67%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-chloro-3-[ethyl(oxan-4-yl)amino]-2-methoxybenzoic acid (111 mg, 0.35 mmol) in DMF (3 ml) at room temperature under nitrogen was added PyBOP (220 mg, 0.42 mmol) followed by N-ethyl-N-(propan-2-yl)propan-2-amine (92 μl, 0.53 mmol) and 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one (89%, 66 mg, 0.39 mmol). After stirring for 1.5 hours at room temperature no starting material was observed by LCMS. Deionized water (20 ml) was added to the reaction mixture and the resultant precipitate was collected by filtration. The solid was washed with deionized water (3×5 ml) before being air dried. The solid was further purified by FCC (5 g silica, Isolute cartridge, gradient of eluents; 100% DCM to 97:3 DCM:MeOH). The sample was dried in a vacuum oven for 18 hours to give 105 mg (64%) the title compound as an off-white solid. LC-MS 98%, m/z=449.5/452.1, 1H NMR (500 MHz, Chloroform-d) δ ppm 11.47 (s, 1H), 8.79 (t, J=5.8 Hz, 1H), 7.73 (d, J=2.6 Hz, 1H), 7.05 (d, J=2.6 Hz, 1H), 5.92 (s, 1H), 4.55 (d, J=6.0 Hz, 2H), 3.98 (dd, J=11.3, 3.8 Hz, 2H), 3.78 (s, 3H), 3.35 (t, J=11.6 Hz, 3H), 3.12 (q, J=7.0 Hz, 2H), 2.42 (s, 3H), 2.28 (s, 3H), 1.92-1.61 (m, 4H), 0.94 (t, J=7.0 Hz, 3H).

후처리

  1. filtrationthe resultant precipitate was collected by filtration
  2. washThe solid was washed with deionized water (3×5 ml)
  3. customdried
  4. customThe solid was further purified by FCC (5 g silica, Isolute cartridge, gradient of eluents; 100% DCM to 97:3 DCM:MeOH)
  5. customThe sample was dried in a vacuum oven for 18 hours

출처 및 근거

ORD 기록
ord-3bc072aa35324da4a3c8f129a998116b
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376422B2

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