Water → HCID 19591404, compound

HRID 849350Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:30][CH2:31]OS(C)(=O)=O)[O:13][C:12](=[O:14])[N:11]([CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:37]([C:44]12[CH2:51][CH2:50][N:47]([CH2:48][CH2:49]1)[CH2:46][CH2:45]2)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O>CN(C=O)C>[OH2:13].[Cl-:1].[CH2:37]([C:44]12[CH2:45][CH2:46][N+:47]([CH2:31][CH2:30][C:9]3([C:4]4[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=4)[O:13][C:12](=[O:14])[N:11]([CH2:15][C:16]4[CH:17]=[C:18]([C:26]([F:27])([F:29])[F:28])[CH:19]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:21]=4)[CH2:10]3)([CH2:50][CH2:51]1)[CH2:48][CH2:49]2)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1.4 g of the compound obtained in step B of EXAMPLE 21 and 0.6 g of 4-benzylquinuclidine in 3 ml of DMF is heated at 80° C. for 2 hours. After cooling to RT, the reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed with water, with 300 ml of 10% HCl solution and with 300 ml of saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum to give 1.35 g of the expected product after crystallization from AcOEt. M.p.=172-175° C.

Workup

temperatureAfter cooling to RT
extractionextracted with AcOEt
washthe organic phase is washed with water, with 300 ml of 10% HCl solution and with 300 ml of saturated NaCl solution
dry with materialdried over MgSO4
customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record: ord-bc4ac6fe2c9d479ca18441f8baeb03de
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011154

Reaction notes

Loading…