Hydrochloric Acid → 3-Benzyloxy-7-(1,1-dioxo-isothiazolidin-2-yl)-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid 4-fluoro-benzylamide

HRID 536143Notes

Reaction equation

[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH:28]=[CH:27][C:26](I)=[CH:25][N:13]3[C:14](=[O:24])[C:15]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:9])=[CH:4][CH:3]=1.[S:32]1(=[O:38])(=[O:37])[CH2:36][CH2:35][CH2:34][NH:33]1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.[Cu]I>[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]3[CH:28]=[CH:27][C:26]([N:33]4[CH2:34][CH2:35][CH2:36][S:32]4(=[O:38])=[O:37])=[CH:25][N:13]3[C:14](=[O:24])[C:15]=2[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The product from Example 26.1.2 (100 mg, 0.189 mmol), isothiazolidine 1,1-dioxide (46 mg, 0.378 mmol), copper(I) iodide (4 mg, 0.019 mmol), N,N-dimethylethyl diamine (3 mg, 0.039 mmol) and potassium carbonate (55 mg, 0.378 mmol) were mixed in DMF (4.0 mL) and heated to 80° C. After 2 h, TLC indicated that the reaction was complete. The reaction mixture was cooled to room temperature and poured into aqueous hydrochloric acid (1.0 M, 40 mL. The resulting solid was collected by filtration and washed with water, dried and subjected to column chromatography (dichloromethane/methanol 50:1) to afford the desired product (93 mg, 95%).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe resulting solid was collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-2c7f489b68eb43d096a09acc0bcc2090
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859563B2

Reaction notes

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