Trifluoroacetic acid → HCID 178460032, 화합물

HRID 577690노트

반응식

HRID 577690 반응식
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13]3[N:21]=[C:20]4[C:16]([N:17]=[CH:18][N:19]4COCC[Si](C)(C)C)=[C:15]([O:30][C:31]4[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=4)[N:14]=3)[CH:9]=[N:8]2)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13]3[N:21]=[C:20]4[C:16]([N:17]=[CH:18][NH:19]4)=[C:15]([O:30][C:31]4[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH:39]=[CH2:40])[CH:34]=[CH:35][CH:36]=4)[N:14]=3)[CH:9]=[N:8]2)[CH2:3]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86679632HCID 86679632, 화합물

생성물 1

HCID 178460032HCID 178460032, 화합물수율 10%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of N-{3-[(2-{[1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-yl]amino}-9-{[2-(trimethylsilyl)ethoxy]methyl}-9H-purin-6-yl)oxy]phenyl}prop-2-enamide (271 mg, 0.471 mmol) in DCM (5.89 mL) was added TFA (1.81 mL, 23.6 mmol). The resulting solution was stirred at rt overnight, then concentrated and dried under vacuum. The resulting residue was taken up in water and neutralized with NaHCO3 to get a slightly sticky suspension. The solid was filtered off, washed with water, dried, and collected to give the crude product, which was purified by SFC to afford the title compound (21 mg, 10 yield) as a lyophilized solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.80 (br. s., 1H) 10.37 (br. s., 1H) 9.20 (br. s., 1H) 8.01-8.11 (m, 1H) 7.61-7.78 (m, 1H) 7.48 (br. s., 1H) 7.37 (d, J=6.32 Hz, 1H) 7.03 (d, J=7.33 Hz, 2H) 6.36-6.59 (m, 1H) 6.20-6.34 (m, 1H) 5.77 (dd, J=10.23, 1.89 Hz, 1H) 4.57 (br. s., 1H) 3.99-4.27 (m, 1H) 3.65-3.94 (m, 3H) 3.00 (br. s., 2H) 2.79 (m, J=15.66 Hz, 1H) 2.00 (br. s., 1H) 1.23 (s, 1H). m/z (APCI+) for C22H23N9O2 446.05 (M+H)+.

후처리

  1. concentrationconcentrated
  2. customdried under vacuum
  3. customto get a slightly sticky suspension
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customdried
  7. customcollected
  8. customto give the crude product, which
  9. customwas purified by SFC

출처 및 근거

ORD 기록
ord-f17d8639c0a248ba8eed55692627ffa0
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040547B2

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