Threoninol → (2R,3R)-2-(1,3-dihydroxybut-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine

HRID 2363687노트

반응식

[OH:1][CH2:2][C@H:3]([NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:17][CH:16]=2)[N:10]2[N:27]=[CH:28][C:29]([CH:30]([CH3:32])[CH3:31])=[C:9]2[N:8]=1)[CH2:4][CH3:5].N[C@H](CO)[C@@H](C)[OH:36]>>[OH:1][CH2:2][C@@H:3]([NH:6][C:7]1[N:12]=[C:11]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[CH:19][CH:20]=2)[N:10]2[N:27]=[CH:28][C:29]([CH:30]([CH3:31])[CH3:32])=[C:9]2[N:8]=1)[C@H:4]([OH:36])[CH3:5]

참가 물질

반응물 2

HCID 2033049Threoninol

HCID 46910588(2R)-2-[[8-isopropyl-4-[[4-(2-pyridyl)phenyl]methylamino]pyrazolo[1,5-a][1,3,5]triazin-2-yl]amino]butan-1-ol

생성물 1

HCID 46910764(2R,3R)-2-(1,3-dihydroxybut-2-ylamino)-8-isopropyl-4-[4-(pyridin-2-yl)benzylamino]pyrazolo[1,5-a]-1,3,5-triazine수율 43%

실험 절차

According to the same conditions resulting in the preparation of the compound 2, the compound 12 is prepared from IIa.2 by oxidation reaction of the sulfur atom and then introduction of L-threoninol. Yield=43%. Oil. 1H NMR (300 MHz, CDCl3): δ 8.69 (d, 1H, J=4.7 Hz, Harom), 7.97 (d, 2H, J=8.3 Hz, Harom), 7.78-7.69 (m, 2H, Harom), 7.63 (8, 1H, Harom), 7.45 (d, 2H, J=8.3 Hz, Harom), 7.26-7.21 (m, 1H, Harom), 6.75 (bs, 1H, NH), 5.63 (d, 1H, J=5.8 Hz, NH), 4.77 (d, 2H, J=6.0 Hz, CH2), 4.22-4.15 (m, 1H, CH), 3.97-3.84 (m, 3H, CH+CH2), 3.01 (hept, 1H, J=7.0 Hz, CH), 1.29 (d, 3H, J=6.2 Hz, CH3), 1.28 (d, 6H, J=7.0 Hz, 2 CH3). MS (ESI): m/z 448 (MH+).

출처 및 근거

ORD 기록: ord-e03b4d94063d450eabc3d27671d1d920
출처 데이터셋: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08691982B2

반응 노트

불러오는 중…