N'-(2-Amino-7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide → 7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

HRID 2239815

반응식

HRID 2239815 반응식
[NH2:1][C:2]1[N:3]=[C:4]([NH:27][NH:28][C:29]([C:31]2[O:32][CH:33]=[CH:34][CH:35]=2)=O)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=4[F:26])[CH2:15][CH2:14]3)[C:6]=2[N:7]=1>C[Si](N[Si](C)(C)C)(C)C>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[N:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][N:8]2[C:6]3[N:7]=[C:2]([NH2:1])[N:27]4[N:28]=[C:29]([C:31]5[O:32][CH:33]=[CH:34][CH:35]=5)[N:3]=[C:4]4[C:5]=3[CH:10]=[CH:9]2)[CH2:14][CH2:15]1

참가 물질

3

반응물 1

HCID 68414926N'-(2-Amino-7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide

생성물 1

HCID 250207657-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

시약·촉매·용매 1

HCID 13838Hexamethyldisilazane용매

반응 조건

온도
120 °C

실험 절차

The title B compound, N′-(2-amino-7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide (53 mg, 0.11 mmol) is dissolved in 0.5 mL of HMDS and 0.5 mL in BSA. The mixture is heated at 120° C. for 16 h, then cooled to RT and evaporated to dryness. The residue is stirred in a mixture of DCM and 6N aqueous HCl for an hour at RT, then the pH is adjusted to 9 with 1M aqueous NaOH. The organic phase is collected and the aqueous phase extracted with additional DCM. The combined organic extracts are dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography, eluting with 3% MeOH in DCM affords 7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine as an off-white solid: LC/MS (M+1=465.2). 1H NMR (CDCl3) δ 3.01 (m, 2H), 3.25 (m, 2H), 3.39 (m, 2H), 3.52 (m, 4H), 4.86 (t, 2H, J=6.6 Hz), 5.76 (br s, 2H), 6.54 (dd, 1H, J=1.8 Hz and 3.4 Hz), 6.8-6.72 (m, 3H), 7.11 (dd, 1H, J=4.6 Hz), 7.19 (m, 2H), 7.57 (t, 1H, J=0.8 Hz).

후처리

  1. temperaturecooled to RT
  2. customevaporated to dryness
  3. customThe organic phase is collected
  4. extractionthe aqueous phase extracted with additional DCM
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by flash chromatography
  9. washeluting with 3% MeOH in DCM

출처 및 근거

ORD 기록
ord-6428fb202f9242ff9c9970d7e77c6fed
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723343B2

연결된 노트

불러오는 중…