Hydrochloride methanol → HCID 58770700, 화합물

HRID 657262노트

반응식

HRID 657262 반응식
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH2:25][CH2:26][CH2:27][O:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.Cl.CO.[N+](C1C=CC(OC(=O)[NH:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH:55]([CH3:57])[CH3:56])=[CH:50][CH:49]=2)=CC=1)([O-])=O>>[CH:55]([O:54][C:51]1[CH:52]=[CH:53][C:48]([NH:47][C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[C:23]4[C:18](=[CH:19][C:20]([O:24][CH2:25][CH2:26][CH2:27][O:28][S:29]([CH3:32])(=[O:31])=[O:30])=[CH:21][CH:22]=4)[N:17]=[CH:16][N:15]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:49][CH:50]=1)([CH3:57])[CH3:56]

참가 물질

4

반응물 3

HCID 21893726Hydrochloride methanolHCID 58769998(4-Isopropoxy-phenyl)-carbamic acid 4-nitrophenyl esterHCID 86609627HCID 86609627, 화합물

생성물 1

HCID 58770700HCID 58770700, 화합물수율 75%

실험 절차

To 4-[7-(3-methanesulfonyloxy-propoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.1 mmol), prepared as described in Example 115, was added 3M HCl/MeOH (2 mL) and the mixture was stirred at rt for 2 h and then concentrated in vacuo and the residue was dissolved in a 1:1 mixture of DCM:MeOH, neutralized with excess Et3N and treated with (4-isopropoxy-phenyl)-carbamic acid 4-nitrophenyl ester (0.11 mmol), which was prepared as described in Example 1a. The mixture was stirred at rt overnight and then concentrated in vacuo and partitioned between water and DCM. DCM layer was drawn off, washed with water thrice, then dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by Preparative TLC (silica gel; DCM:MeOH; 9.5:0.5) to obtain 40 mg (75%) of the title compound. 1H-NMR (300 MHz, CDCl3): 9.12 (s, 1H), 8.05 (d, 1H), 7.32-7.20 (m, 4H), 6.81 (d, 2H), 6.53 (s, 1H), 4.50-4.40 (m, 3H), 4.25 (t, 4H), 3.72-3.59 (m, 1H), 3.16-3.03 (m, 2H), 3.01 (s, 3H), 2.36-2.26 (m, 2H), 2.18-2.00 (m, 2H), 1.99-1.87 (m, 2H), 1.29 (d, 6H). LC/MS (ESI): 543.1 (MH)+.

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue was dissolved in a 1:1 mixture of DCM
  3. customwas prepared
  4. stirringThe mixture was stirred at rt overnight
  5. concentrationconcentrated in vacuo
  6. custompartitioned between water and DCM
  7. washwashed with water thrice
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by Preparative TLC (silica gel; DCM:MeOH; 9.5:0.5)

출처 및 근거

ORD 기록
ord-a62f7c8273b74cee9a253ab31534da0b
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071768B2

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