Diisopropylethylamine → 3-(1,3-Dioxolan-2-yl)propyl 1-(4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)-carbonyl)amino)methyl)phenoxy)methyl)benzoyl)piperidine-4-carboxylate

HRID 874811노트

반응식

HRID 874811 반응식
[C:1]1([C@H:7]([NH:25][C:26]([O:28][C@@H:29]2[CH:34]3[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]3)[CH2:30]2)=[O:27])[C:8]2[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=2)[O:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH:71]1[CH2:76][CH2:75][CH:74]([C:77]([O:79][CH2:80][CH2:81][CH2:82][CH:83]2[O:87][CH2:86][CH2:85][O:84]2)=[O:78])[CH2:73][CH2:72]1>CN(C=O)C.C(OCC)(=O)C>[C:1]1([C@H:7]([NH:25][C:26]([O:28][C@@H:29]2[CH:34]3[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]3)[CH2:30]2)=[O:27])[C:8]2[CH:9]=[C:10]([CH:22]=[CH:23][CH:24]=2)[O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([N:71]3[CH2:76][CH2:75][CH:74]([C:77]([O:79][CH2:80][CH2:81][CH2:82][CH:83]4[O:84][CH2:85][CH2:86][O:87]4)=[O:78])[CH2:73][CH2:72]3)=[O:18])=[CH:20][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867208154-((3-((S)-Phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)-phenoxy)methyl)benzoic acidHCID 867223013-(1,3-Dioxolan-2-yl)propyl piperidine-4-carboxylate hydrochloride

생성물 1

HCID 867223033-(1,3-Dioxolan-2-yl)propyl 1-(4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)-carbonyl)amino)methyl)phenoxy)methyl)benzoyl)piperidine-4-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoic acid (0.300 g, 0.57 mmol) in DMF (2.5 mL) was added di-iso-propylethylamine (0.40 mL, 2.29 mmol) and HATU (0.262 g, 0.69 mmol) and the mixture stirred at RT for 30 minutes. To the resultant solution was added a solution of 3-(1,3-dioxolan-2-yl)propyl piperidine-4-carboxylate hydrochloride (0.241 g, 0.86 mmol) in DMF (1.8 mL). The mixture was stirred at RT for 18 hours. The mixture was diluted with ethyl acetate, washed with 10% aqueous potassium carbonate, brine (×2), dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was used directly in the next step with no further purification.

후처리

  1. stirringThe mixture was stirred at RT for 18 hours
  2. washwashed with 10% aqueous potassium carbonate, brine (×2)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customthe solvent evaporated at reduced pressure
  6. customThe residue was used directly in the next step with no further purification

출처 및 근거

ORD 기록
ord-8b8aa91656ed4a8494a2e8c2ab8a2e68
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980913B2

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