Trifluoroacetic acid → 5-(4-phenoxyphenyl)-7-(4-piperidyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 51524

반응식

HRID 51524 반응식
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:17]([C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[CH:9]=2)=[CH:16][CH:15]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 22736379tert-butyl4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-piperidinecarboxylate

생성물 1

HCID 101615435-(4-phenoxyphenyl)-7-(4-piperidyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine수율 92.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-piperidinecarboxylate (0.69 g, 1.4 mmol) in dry CH2Cl2 (25 ml) at 0° C. was added TFA (5 ml). The solution was stirred at room temperature for 20 hr and the solvent evaporated. NaOH solution (5N, 10 ml) was added and the resulting slurry was extracted with EtOAc (3×50 ml). Wash with brine (1×50 ml). Dry, filter and concentrate to leave a solid which was triturated with diethylether and filtered to leave 5-(4-phenoxyphenyl)-7-(4-piperidyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (433258) as a white solid (500 mg, 91%). M.pt 209-211° C. Rf in 1:1 EtOAc : MeOH=0.1. 1H NMR (d6 DMSO, 250 MHz) 8.13 (1H, s), 7.36-7.48 (4H, m), 7.29 (1H, s), 7.04-7.16 (5H, m), 5.80 (2H, bs), 4.64 (1H, m), 3.10 (2H, m), 2.80 (1H, bs), 2.67 (2H, m), 1.94 (4H, m). Mass spec. C23H23ON5 (385.1902). IR (KBr disc): 3278, 1620, 1585, 1490, 1245 cm−1.

후처리

  1. customthe solvent evaporated
  2. additionNaOH solution (5N, 10 ml) was added
  3. extractionthe resulting slurry was extracted with EtOAc (3×50 ml)
  4. washWash with brine (1×50 ml)
  5. customDry
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto leave a solid which
  9. customwas triturated with diethylether
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-05cff2dd24b34503aed78dae107a8f09
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713474B2

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