Hydrochloric Acid → HCID 178457041, 화합물

HRID 511628노트

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HRID 511628 반응식
Cl.[Cl:2][C:3]1[C:4]([C:51]([F:54])([F:53])[F:52])=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][CH:12]3[CH2:15][CH:14]([CH2:16][N:17]([CH2:21][C@@H:22]4[C@H:26]5[O:27]C(C)(C)[O:29][C@H:25]5[C@H:24]([N:32]5[C:36]6[N:37]=[CH:38][N:39]=[C:40]([NH2:41])[C:35]=6[CH:34]=[CH:33]5)[CH2:23]4)[CH:18]([CH3:20])[CH3:19])[CH2:13]3)[N:8](COCC[Si](C)(C)C)[C:7]=2[CH:50]=1>CO>[NH2:41][C:40]1[C:35]2[CH:34]=[CH:33][N:32]([C@@H:24]3[CH2:23][C@H:22]([CH2:21][N:17]([CH2:16][CH:14]4[CH2:15][CH:12]([CH2:11][C:9]5[NH:8][C:7]6[CH:50]=[C:3]([Cl:2])[C:4]([C:51]([F:53])([F:52])[F:54])=[CH:5][C:6]=6[N:10]=5)[CH2:13]4)[CH:18]([CH3:20])[CH3:19])[C@@H:26]([OH:27])[C@H:25]3[OH:29])[C:36]=2[N:37]=[CH:38][N:39]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 677763577-[(3aS,4R,6R,6aR)-6-({[(3-{[6-chloro-5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]methyl}cyclobutyl)methyl](propan-2-yl)amino]methyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

생성물 1

HCID 178457041HCID 178457041, 화합물수율 27%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
40 °C

실험 절차

12N HCl (1.5 ml) was added slowly to a solution of 7-[(3aS,4R,6R,6aR)-6-({[(3-{[6-chloro-5-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,3-benzodiazol-2-yl]methyl}cyclobutyl)methyl](propan-2-yl)amino]methyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (174 mg, 0.22 mmol) in MeOH (1.5 ml) and stirred at 40° C. for 6 h. The reaction was monitored by LCMS, no starting material seen after 2.5 h. The reaction mixture was concentrated in vacuo, then basified with 7N NH3 in MeOH (5 ml). This was then evaporated to dryness. Purification by silica gel column chromatography, eluting with 7N NH3 in MeOH:DCM (1:9) gave the desired product (36 mg, 27%) as a white solid; MS (ESI+) for C29H35ClF3N7O2 m/z 606.30 [M+H]+; HPLC purity 100% (ret. time, 2.59 min); 1H NMR (500 MHz, MeOD) δH ppm 0.93-1.09 (6H, m), 1.41-1.64 (2H, m), 1.76-2.06 (1H, m), 2.15-2.65 (9H, m), 2.65-2.88 (1H, m), 2.91-3.13 (3H, m), 3.80-4.09 (1H, m), 4.19-4.46 (1H, m), 4.88-4.94 (1H, m), 6.46-6.77 (1H, m), 7.19 (1H, d, J=3.63 Hz), 7.69 (1H, s), 7.89 (1H, s), 8.06 (1H, s)

후처리

  1. waitno starting material seen after 2.5 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThis was then evaporated to dryness
  4. customPurification by silica gel column chromatography
  5. washeluting with 7N NH3 in MeOH:DCM (1:9)

출처 및 근거

ORD 기록
ord-fa059c69b8394fcb86af2b283162943c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096634B2

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