Triethylamine → HCID 23568903, compound

HRID 2376255Notes

Reaction equation

C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)[N:19]=[C:18]([CH2:29][OH:30])[CH:17]=2)[CH:12]=[CH:13][C:14]=1[Cl:15].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C1COCC1.C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2[N:20]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)[N:19]=[C:18]([CH2:29][O:30][S:32]([CH3:31])(=[O:34])=[O:33])[CH:17]=2)[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

Conditions

Temperature: 35 °C

Procedure

Triethylamine (3.25 L, 23.3 mol) was added to a solution containing [5-(3,4-dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]-methanol (Example 516, 5.18 kg, 14.8 mol) in THF (25.2 L) and toluene (6.3 L) at rt under N2. The reaction mixture was heated to 35° C. and methanesulfonyl chloride (1.82 L, 23.5 mol) was added slowly maintaining the temperature between 35-45° C. The reaction mixture was stirred for an additional 2 h at 45° C. When HPLC analysis indicated the disappearance of the starting material, the reaction mixture was cooled to rt and quenched with 10% aq. NaCl (6.3 L). The organic layer was washed with brine (5.0 L) and the desired mesylate was used in solution in the next synthetic step without isolation. Data compared favorably with that obtained for Example 1, Step D.

Workup

temperaturemaintaining the temperature between 35-45° C
temperaturethe reaction mixture was cooled to rt
customquenched with 10% aq. NaCl (6.3 L)
washThe organic layer was washed with brine (5.0 L)
customthat obtained for Example 1, Step D

Sources & evidence

ORD record: ord-3bf17f39c8cf4170baca833720e138ff
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465808B2

Reaction notes

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