Triethylamine → (R)-Quinuclidin-3-yl ((S)-(3-((3-((4,4-diethoxybutyl)carbamoyl)-1-methyl-1H-pyrazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate

HRID 877329노트

반응식

HRID 877329 반응식
[CH3:1][N:2]1[C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C@H:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:16][C:17]([O:19][C@@H:20]3[CH:25]4[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]4)[CH2:21]3)=[O:18])[CH:10]=2)=[CH:5][C:4]([C:34](O)=[O:35])=[N:3]1.C(N(CC)CC)C.[CH2:44]([O:46][CH:47]([O:52][CH2:53][CH3:54])[CH2:48][CH2:49][CH2:50][NH2:51])[CH3:45].CCN=C=NCCCN(C)C.OC1C=CC=C[N+]=1[O-]>CN(C=O)C.C(OCC)(=O)C>[N:22]12[CH2:27][CH2:26][CH:25]([CH2:24][CH2:23]1)[C@@H:20]([O:19][C:17](=[O:18])[NH:16][C@H:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:6]3[N:2]([CH3:1])[N:3]=[C:4]([C:34](=[O:35])[NH:51][CH2:50][CH2:49][CH2:48][CH:47]([O:46][CH2:44][CH3:45])[O:52][CH2:53][CH3:54])[CH:5]=3)[CH:10]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:21]2

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 806724,4-DiethoxybutylamineHCID 867208301-methyl-5((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)-methyl)-1H-pyrazole-3-carboxylic acidHCID 178526252HCID 178526252, 화합물

생성물 1

HCID 90211958(R)-Quinuclidin-3-yl ((S)-(3-((3-((4,4-diethoxybutyl)carbamoyl)-1-methyl-1H-pyrazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate수율 57%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 1-methyl-5-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)-1H-pyrazole-3-carboxylic acid (0.30 g, 0.61 mmol) in DMF (6 mL) was added triethylamine (0.2 mL, 1.53 mmol), 4-aminobutyraldehyde diethyl acetal (0.20 mL, 1.22 mmol), EDCI (0.18 g, 0.91 mmol) and 2-hydroxypyridine-N-oxide (0.09 g, 0.91 mmol). The reaction mixture stirred at RT for 90 h. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate, brine, dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure to afford the crude target material (0.22 g, 57%) which was used directly without further purification.

후처리

  1. washwashed with saturated sodium hydrogen carbonate, brine
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. customthe solvent evaporated at reduced pressure

출처 및 근거

ORD 기록
ord-f9f2c2bc164e4d6bbfb164213a227c6c
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987299B2

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