Acetonitrile → HCID 89616010, 화합물

HRID 882118노트

반응식

HRID 882118 반응식
[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:11]3[C:12]4[C:19]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])=[CH:18][N:17](COCC[Si](C)(C)C)[C:13]=4[N:14]=[CH:15][N:16]=3)[CH:7]=[CH:8]2)=[N:3]1.C(O)(C(F)(F)F)=O.C(#N)C.[OH-].[NH4+]>C(Cl)Cl>[CH3:1][N:2]1[CH:10]=[C:9]2[C:4]([CH:5]=[C:6]([C:11]3[C:12]4[C:19]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])=[CH:18][NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH:7]=[CH:8]2)=[N:3]1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 89630017HCID 89630017, 화합물

생성물 1

HCID 89616010HCID 89616010, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Prop-2-en-1-yl 4-(2-methyl-2H-indazol-6-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate was dissolved in DCM (1.0 mL) and then TFA (0.91 mL, 12 mmol) was added. The resulting solution was stirred for 2 hours at room temperature before being concentrated in vacuo. Acetonitrile (0.50 mL) and ammonium hydroxide (0.50 mL, 3.6 mmol) were added to the residue and the solution was heated to 50° C. for 3 hours. The reaction was concentrated in vacuo and purified by reverse phase chromatography using a 5-35% acetonitrile gradient in water with 0.1% TFA modifier. Pure fractions were free-based by extracting from a saturated sodium bicarbonate solution using 3:1 CHCl3:IPA (×3). The combined organic layers were then washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford prop-2-en-1-yl 4-(2-methyl-2H-indazol-6-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate as a white solid. LRMS (ESI) calcd for C18H16N5O2 [M+H]+: 334, found 334. 1H NMR (600 MHz, DMSO-D6) δ 13.04 (s, 1H), 8.96 (s, 1H), 8.43 (s, 1H), 8.39 (s, 1H), 7.81 (m, 1H), 7.79 (dd, 1H, J=8.4, 0.8 Hz), 7.39 (dd, 1H, J=8.4, 1.4 Hz), 5.5 (m, 1H), 4.97-5.04 (m, 2H), 4.30 (dm, 2H, J=5.7 Hz), 4.25 (s, 3H).

후처리

  1. concentrationbefore being concentrated in vacuo
  2. temperaturethe solution was heated to 50° C. for 3 hours
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified by reverse phase chromatography
  5. extractionby extracting from a saturated sodium bicarbonate solution
  6. washThe combined organic layers were then washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-76a57905b1bc407f8d2d215852b8adb8
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993756B2

반응 노트

불러오는 중…