Water → HCID 59175897, compound

HRID 1807791Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:16])OC2C=CC=CC=2)=[CH:3][CH:2]=1.[NH2:17][C:18]1[CH:47]=[CH:46][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]([OH:45])([C:41]([F:44])([F:43])[F:42])[C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)[CH2:25][CH2:24]2)=[CH:20][C:19]=1[F:48].O.ClCCl>O1CCOCC1>[F:48][C:19]1[CH:20]=[C:21]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]([OH:45])([C:37]([F:38])([F:39])[F:40])[C:41]([F:43])([F:44])[F:42])=[CH:32][CH:31]=3)[CH2:25][CH2:24]2)[CH:46]=[CH:47][C:18]=1[NH:17][C:8]([NH:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)=[O:16]

Participants

Conditions

Temperature: 130 °C

Procedure

Phenyl pyridin-4-ylcarbamate (0.461 mmol, 0.099 g) was added to a stirred solution of 2-(4-((4-(4-amino-3-fluorobenzyl)piperazin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.279 mmol, 0.139) in dioxane (7 mL) and mixture heated in a microwave reactor for 10 minutes at 130° C. Water (10 mL) was added to the reaction followed by dichloromethane (10 ml). The organic layer was separated, washed with water (3×10 mL), dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by preparative HPLC giving the title compound (0.023 g). MS (ESI) m/z 586.3 [M+H]+

Workup

customThe organic layer was separated
washwashed with water (3×10 mL)
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-963215e5989e4710acc908a0d21473be
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357679B2

Reaction notes

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