Triethylamine → 6-(3-(1H-imidazol-2-yl)piperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine

HRID 1049924노트

반응식

HRID 1049924 반응식
[NH2:1][C:2]1[C:3]2[N:11]=[C:10](C3C=C(C=C(F)C=3)C(NCC3CCN(C)CC3)=O)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl.[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]1[CH2:41][CH2:40][CH2:39][NH:38][CH2:37]1.C(N(CC)CC)C.CC(N(C)C)=O>ClCCl>[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]1[CH2:41][CH2:40][CH2:39][N:38]([C:10]2[CH:9]=[CH:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=3[N:11]=2)[CH2:37]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 31374DimethylacetamideHCID 679965363-(1H-imidazol-2-yl)piperidine hydrochlorideHCID 727035233-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluoro-N-((1-methylpiperidin-4-yl)methyl)benzamide

생성물 1

HCID 727039236-(3-(1H-imidazol-2-yl)piperidin-1-yl)pyrido[3,2-d]pyrimidin-4-amine수율 8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

To an 8 mL screw-cap vial was added 6-chloropyrido[3,2-d]pyrimidin-4-amine 10 (1 equiv., 0.68 mmol, 123 mg), 3-(1H-imidazol-2-yl)piperidine hydrochloride (1 equiv., 0.68 mmol, 128 mg), triethylamine (3 equiv., 2.05 mmol, 0.287 mL) and DMA (2 mL). The reaction was capped and shaken at 100° C. overnight. The reaction was then cooled to room temperature, diluted with dichloromethane, and washed with water. The organic was then concentrated, then purified by reverse phase HPLC, yielding 16 mg of product. 1H NMR (400 MHz, DMSO) δ 8.20-8.14 (m, 3H), 7.82-7.77 (m, 1H), 7.54-7.49 (d, J=9.4 Hz, 1H), 7.38-7.28 (d, J=8.1 Hz, 2H), 6.96-6.94 (s, 2H), 4.79-4.71 (d, J=12.7 Hz, 1H), 4.53-4.46 (d, J=17.4 Hz, 1H), 3.17-3.07 (m, 1H), 3.07-2.96 (m, 1H), 2.96-2.84 (m, 1H), 2.18-2.08 (m, 1H), 1.91-1.77 (m, 2H), 1.66-1.51 (m, 1H). LCMS M/Z (M+H)=296.

후처리

  1. customTo an 8 mL screw-cap vial
  2. customThe reaction was capped
  3. temperatureThe reaction was then cooled to room temperature
  4. washwashed with water
  5. concentrationThe organic was then concentrated
  6. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-eb9212c002f64c099a0e8fde9506ae6f
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382241B2

반응 노트

불러오는 중…