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Hydrochloric Acid → 5-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(4-piperidinyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 1910006
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HRID 1910006 반응식
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16]([C:20](=[O:30])[CH2:21][C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3[F:29])[CH2:15][CH2:14]4)=[CH:9][N:8]([CH:31]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)[C:4]=2[N:5]=[CH:6][N:7]=1.Cl.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>O1CCOCC1>[F:29][C:23]1[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=1[CH2:21][C:20]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([C:10]3[C:3]4[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=4[N:8]([CH:31]4[CH2:32][CH2:33][NH:34][CH2:35][CH2:36]4)[CH:9]=3)=[CH:19][CH:18]=2)[CH2:14][CH2:15]1)=[O:30]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 668236061,1-dimethylethyl 4-(4-amino-5-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-piperidinecarboxylate

생성물 1

HCID 668236445-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(4-piperidinyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine수율 82%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To 1,1-dimethylethyl 4-(4-amino-5-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-piperidinecarboxylate (180 mg, 0.306 mmol) was added HCl (4 mL, 16.00 mmol) 4M in dioxane. The reaction was let stir at room temp overnight. The reaction was concentrated then diluted with diethyl ether and filtered to isolate 5-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-7-(4-piperidinyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (140 mg, 0.249 mmol, 82% yield) as a light yellow solid as the dihydrochloride salt. LC/MS (ES) m/z=489.0 [M+H]+. 1H NMR (400 MHz, METHANOL-d4) δ 8.39 (s, 1H), 8.24 (d, J=8.34 Hz, 1H), 7.61 (s, 1H), 7.44 (s, 1H), 7.32-7.37 (m, 1H), 7.04-7.20 (m, 3H), 5.08-5.18 (m, 1H), 4.36 (t, J=8.46 Hz, 2H), 3.99 (s, 2H), 3.68 (s, 3H), 3.65 (d, J=13.89 Hz, 2H), 3.36-3.40 (m, 2H), 2.41-2.53 (m, 2H), 2.37 (d, 2H).

후처리

  1. concentrationThe reaction was concentrated
  2. additionthen diluted with diethyl ether
  3. filtrationfiltered

출처 및 근거

ORD 기록
ord-39d3a88f0d8342a3bb72973e02ba3698
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08598156B2

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