(3R)-1-azabicyclo[2.2.2]octan-3-yl carbonochloridate hydrochloride → [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-chloro-N-[(3R)-quinuclidin-3-yl]oxycarbonyl-anilino)methyl]benzoate

HRID 1497992Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N+:4]([O-:39])[CH:5]=[C:6]([Cl:38])[C:7]=1[CH2:8][C@H:9]([O:20][C:21](=[O:37])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:36])[CH:23]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.Cl.[C:41](Cl)(=[O:51])[O:42][C@@H:43]1[CH:48]2[CH2:49][CH2:50][N:45]([CH2:46][CH2:47]2)[CH2:44]1>CC#N>[Cl:38][C:6]1[CH:5]=[N+:4]([O-:39])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@H:9]([O:20][C:21](=[O:37])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([C:41]([O:42][C@@H:43]2[CH:48]3[CH2:49][CH2:50][N:45]([CH2:46][CH2:47]3)[CH2:44]2)=[O:51])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Cl:36])[CH:23]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]3-[(2-chloroanilino)methyl]benzoate (72 mg, 0.123 mmol) and (R)-quinuclidin-3-yl carbonochloridate hydrochloride (138 mg, 0.612 mmol) in anhydrous CH3CN (1 mL) was heated at 80° C. for 3 minutes under microwave irradiation. After cooling to room temperature, the solvent was removed in vacuo. Purification of the crude material by preparative HPLC afforded the title compound as a yellow solid (47.8 mg, 53%).

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed in vacuo
customPurification of the crude material by preparative HPLC

Sources & evidence

ORD record: ord-b1a7690c1fe048049826f484a9a527e3
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199980B2

Reaction notes

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