6-(5-chloro-2-fluoropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine → HCID 178508356, 화합물

HRID 1623387

반응식

HRID 1623387 반응식
[Cl:1][C:2]1[C:3]([C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:12]([NH2:23])=[N:11][CH:10]=2)=[CH:4][C:5](F)=[N:6][CH:7]=1.[C@H:24]1([NH2:31])[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26][CH2:25]1>CS(C)=O>[NH2:30][C@H:27]1[CH2:28][CH2:29][C@H:24]([NH:31][C:5]2[CH:4]=[C:3]([C:9]3[N:14]=[C:13]([NH:15][CH2:16][CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:12]([NH2:23])=[N:11][CH:10]=3)[C:2]([Cl:1])=[CH:7][N:6]=2)[CH2:25][CH2:26]1

참가 물질

4

반응물 2

HCID 669371366-(5-chloro-2-fluoropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamineHCID 178511674HCID 178511674, 화합물

생성물 1

HCID 178508356HCID 178508356, 화합물수율 49.9%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
100 °C

실험 절차

To a scintillation vial containing 6-(5-chloro-2-fluoropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine (17 mg, 0.050 mmol) was added DMSO (1.3 ml) and trans-cyclohexane-1,4-diamine R2 (57.5 mg, 0.503 mmol). The homogenous reaction mixture was capped and heated to 100° C. in a oil bath for 16 hr. The reaction mixture was purified by reverse phase preparative HPLC to yield 6-(2-(trans-4-aminocyclohexylamino)-5-chloropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine (13.7 mg, 0.025 mmol, 49.9% yield), LCMS (m/z): 432.1 (MH+), retention time=0.41 min as a TFA salt after lypholyzing. 1H NMR (400 MHz, METHANOL-d4) d ppm 1.30-1.50 (m, 4H) 1.51-1.65 (m, 2H) 1.69-1.78 (m, 2H) 1.93-2.06 (m, 1H) 2.07-2.24 (m, 4H) 3.10-3.19 (m, 1H) 3.36-3.45 (m, 2H) 3.48 (d, J=6.65 Hz, 2H) 3.64-3.75 (m, 1H) 3.96 (dd, J=11.35, 3.13 Hz, 2H) 7.04-7.10 (m, 1H) 7.64 (s, 1H) 8.01 (s, 1H).

후처리

  1. customThe homogenous reaction mixture was capped
  2. customThe reaction mixture was purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-322099e20fd44e2c9e78ceee2b3b0464
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778951B2

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