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

HRID 2205707ノート

反応式

HRID 2205707 の反応式
[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>[CH2:53]([O:52][CH:47]([O:46][CH2:44][CH3:45])[CH2:48][CH2:49][CH2:50][NH:51][C:34]([C:4]1[CH:5]=[C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C@@H:15]([NH:16][C:17](=[O:18])[O:19][C@@H:20]3[CH:25]4[CH2:24][CH2:23][N:22]([CH2:27][CH2:26]4)[CH2:21]3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:12]=[CH:13][CH:14]=2)[N:2]([CH3:1])[N:3]=1)=[O:35])[CH3:54]

参加物

8

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-88f5b8e2541c4710ae342d90b45eac06
出典データセット
uspto-grants-2016_06
特許番号
US09371318B2

反応ノート

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