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 1097770Notes

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-2b8326e6dfe042f49e65904c29f6f3d5
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143268B2

Reaction notes

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